As a manager, he has worked for Reggiana, Parma, Juventus, Milan, Chelsea, Paris Saint-Germain, Real Madrid and Bayern Munich, and has won domestic titles in Italy, England, France, Spain and Germany.
Ancelotti began his career in 1974 with Parma. He made his professional debut in Serie C during the 1976–77 season, at the age of 18. Under manager Cesare Maldini, he was often deployed behind the forwards, or as a second striker, due to his eye for goal. Ancelotti excelled in this role and helped Parma to a second place in the Serie C1 girone A during the 1978–79 season, which qualified the team for the Serie B play-offs. In the decisive match in Vicenza, against Triestina, with the score tied at 1–1, he scored two goals, which gave Parma a 3–1 victory and sealed their place in Serie B the following season.
After attracting strong interest from Inter Milan, in the summer of 1979 Ancelotti transferred to Roma, and made his Serie A debut in a 0–0 draw against Milan on 16 September. Under manager Nils Liedholm, he was deployed as a winger or central midfielder and became one of the club's most important players in a team which featured the likes of Brazilian star midfielder Falcão and Italian footballers Roberto Pruzzo, Bruno Conti and Pietro Vierchowod, immediately winning consecutive Coppa Italia titles in his first two seasons with the club. During his eight seasons at the club, he won the Coppa Italia a total of four times (1980, 1981, 1984, and 1986). After struggling with knee injuries, and managing second- and third-place league finishes in 1981 and 1982, Ancelotti helped lead the team to win a historic Italian championship in 1983, the club's second ever league title in their history. The following season, he even helped Roma to win another Coppa Italia title and reach the European Cup final in 1984, although missed the final through injury as Roma were defeated by Liverpool on penalties at the Stadio Olimpico in Rome. He was named the team's captain in 1985 under new club manager Sven-Göran Eriksson, and served as a mentor to the young midfielder Giuseppe Giannini, as Roma won the Coppa Italia, but once again narrowly missed out on the league title during the 1985–86 Serie A season, finishing in second place behind Juventus.
From 1987 until 1992, Ancelotti played for Milan, and was a key part of the successful squad that won the Serie A title in 1988, consecutive European Cups in 1989 and 1990, two European Super Cups, two Intercontinental Cups and a Supercoppa Italiana under manager Arrigo Sacchi. During this time, Milan played with one of their finest teams ever assembled in that decade under the financial backing of club president Silvio Berlusconi, with Paolo Maldini, Franco Baresi, Mauro Tassotti and Alessandro Costacurta as defenders; Frank Rijkaard, Ruud Gullit and Roberto Donadoni as midfielders; and Marco van Basten upfront. One of Ancelotti's most memorable moments with Milan was when he received a pass from Ruud Gullit, dribbled around two Real Madrid players and netted a powerful long-range shot during the Rossoneri's 5–0 thrashing of Real Madrid in the 1989 European Cup semi-finals. He went on to play all 90 minutes in Milan's 4–0 dismantling of Steaua București in the final.
The following season, Ancelotti suffered an injury to his left knee in the quarter-finals of the European Cup against KV Mechelen which forced him to miss the semi-finals, although he was able to return in time to help Milan defend their title against Benfica in the final, held in Vienna. Following Sacchi's departure, he won a second Serie A title under replacement manager Fabio Capello during the 1991–92 Serie A season, as Milan won the title undefeated, but persistent knee injuries and competition from youngster Demetrio Albertini limited his playing time, and eventually forced him into premature retirement at the end of the season, at the age of 33. He played the final match of his career with the club in a 4–0 home win over Hellas Verona on 17 May 1992, in which he came off the bench in the final 20 minutes of the game and scored two goals, and was given an ovation by the fans.
Under manager Enzo Bearzot, Ancelotti made his Italy national team debut and scored his first and only goal on 6 January 1981 in a one-off tournament against the Netherlands, which ended in a 1–1 draw. He was very likely to be capped for the 1982 World Cup campaign, but a dramatic knee injury forced him away for several months, as Italy went on to win the tournament without him. He was a part of Italy's World Cup squad in the 1986 World Cup, where he did not make a single appearance, however.
Under new Italy manager Azeglio Vicini, he was also a key member of the Italy squad that reached the semi-finals of UEFA Euro 1988, and was also set to represent his nation at the Summer Olympics in Seoul that summer. An injury to the meniscus of his right knee, however, prevented him from taking part in the tournament, where Italy ultimately managed a fourth-place finish. Ancelotti later went on to play in the 1990 World Cup on home soil under Vicini at the age of 31, although an injury in the second group match against Austria once again limited his appearances in the competition to just three, and kept him on the sidelines until the third-place final against England, in which he returned to help Italy to a 2–1 win. Ancelotti made a total of 26 performances for the Italian national side, and announced his retirement from international football in 1991, making his final Italy appearance under Arrigo Sacchi.
A world-class player, Ancelotti was a a creative, cautious, and efficient midfielder who was known for his leadership, skill, composure on the ball, and organisational ability; he is regarded as one of the best Italian midfielders of his generation. Although he lacked pace, as well as notable physical and athletic characteristics, he was a highly talented, yet hard-working, combative, and tenacious team-player, who was competent defensively, but who above all possessed excellent technical ability, tactical intelligence, vision and passing range, as well as a powerful and accurate shot from outside the area; his wide range of skills enabled him to contribute to his team's offensive play with goals and assists. A versatile midfielder, he was capable of being deployed in several positions: while he was usually deployed as a playmaker in the centre of the pitch during his time with Milan under Arrigo Sacchi, he often played on the wings during his time with Roma, and was also capable of playing as an attacking midfielder; in his youth, he was often deployed in a more advanced role as a forward, usually as a second striker. As with Milan he was often deployed in front of the back-line, as a central or defensive midfielder, a position which allowed him to set the tempo of his team's play after winning back possession, he is regarded as having been the mentor and predecessor of Demetrio Albertini and Andrea Pirlo in the deep-lying playmaking role at the club. Despite his ability, his career was affected by several injuries, which limited his playing time, and forced him into retirement in 1992.
Ancelotti undertook his coaching studies at Coverciano, where he penned a research article entitled "Il Futuro del Calcio: Più Dinamicità" (English: "The Future of Football: More Dynamism"). After serving as an assistant manager with the Italy national team under his former Milan coach Arrigo Sacchi between 1992 and 1995, and reaching the 1994 World Cup final, Ancelotti began his managerial career with Serie B side Reggiana in 1995, where he immediately aided the team in achieving promotion to Serie A; he left after the 1995–96 Serie B season, finishing with a record of 17 wins, 14 draws, and 10 losses in his only season with the club.
Ancelotti joined Parma the following season, a team which had recently enjoyed several years of domestic and European success under the previous manager Nevio Scala, and which contained several promising young players, including future Italy stars Gianluigi Buffon and Fabio Cannavaro. Ancelotti made his debut in the Coppa Italia in a 3–1 loss to Pescara. Ancelotti made several changes at the club, implementing a rigorous Sacchi-inspired 4–4–2 formation, and initially deploying creative forward Gianfranco Zola out of position on the left wing in order to accommodate Hristo Stoichkov up-front, although both players were later eventually sold by the club after lack of playing time due to struggling to perform in this system. With the new attacking partnership of Enrico Chiesa and Hernán Crespo, Parma finished second in Serie A during the 1996–97 season under Ancelotti, which guaranteed them a place in the next edition of the UEFA Champions League. The following season, the club had agreed to sign another Italian creative forward, Roberto Baggio, but Ancelotti impeded the transfer as he once again did not feel that a player like Baggio would fit into his tactical plans. Ancelotti later stated that he regretted this decision, stating that at the time he believed that the 4–4–2 was the ideal formation for success, and that offensive playmakers were not compatible with this system. After suffering a first round elimination in the 1997–98 Champions League, and a semi–final appearance in the Coppa Italia, Ancelotti was only able to guide Parma to a sixth-place finish in Serie A during the 1997–98 season, and was sacked at the end of the season, despite qualifying the team for next season's UEFA Cup.
In February 1999, Ancelotti was appointed Juventus manager, where he both succeeded and preceded Marcello Lippi, who returned to the club when Ancelotti left. With Juventus, Ancelotti became less rigorous with the team's formation, abandoning his favoured 4–4–2 in order to accommodate star French playmaker Zinedine Zidane in his preferred free role behind the forwards in the team's starting line-up. His first season at Juventus began promisingly, as he immediately won the Intertoto Cup with the club by beating Rennes 4–2 on aggregate, although Juventus suffered a round of 16 elimination in the UEFA Cup, and lost the league title to Lazio by a single point on the final match-day of the season; this was after surrendering a five-point lead with three games remaining, which drew strong criticism from the fans and the board of directors. The following season, Ancelotti went trophyless, finishing runner-up in Serie A yet again, to Roma, and he was sacked by Juventus. Ancelotti's dismissal was announced by Juventus at half-time in the final league game of the season at home against Atalanta, on 17 June 2001, even though they were still within a chance of winning the title; Juventus won the match 2–1, although the result was not enough to prevent them from finishing behind Roma in the league. Ancelotti finished his tenure with Juventus with a record of 63 wins, 33 draws and 18 losses.
Ancelotti was appointed Milan manager on 5 November 2001, after Fatih Terim was sacked due to poor results. He was inheriting another recently trophyless team in Milan, as the Rossoneri had floundered domestically and in Europe since their last Scudetto victory in 1999. In the 2001–02 season, Ancelotti led Milan to qualify for the Champions League once again, as the team managed a fourth-place finish in Serie A, and also reached semi-finals of the UEFA Cup, their best ever finish in the competition, losing out to Borussia Dortmund, and also suffered a semi-final elimination in the Coppa Italia to Juventus.
The following season, Ancelotti, who was heavily criticised by club owner Silvio Berlusconi due to his supposedly defensive tactics, was able to adopt a creative play in Milan while making several changes to the team's roster. He made Dida, still maligned for his 2000–01 Champions League howler against Leeds United, his new starting goalkeeper barely a month into the 2002–03 season, while converting budding attacking midfielder Andrea Pirlo to a defensive midfielder, and played him behind the number 10, either Rui Costa or Rivaldo, in front of the team's back-line, as a deep-lying playmaker in a 4–3–1–2 or 4–1–2–1–2 formation. At the same time, Filippo Inzaghi and Andriy Shevchenko proved to be dominant and dynamic strikers, who were prolific in front of goal.
Milan won the 2003 Champions League final, beating Juventus 3–2 on penalties at Old Trafford, and also won the 2003 Coppa Italia Final over Roma. It was a sweet revenge for him as Juventus had brutally sacked him and to add insult, Marcello Lippi was re-hired for a second tenure and won back-to-back Serie A titles. The following season, with the addition of Brazilian attacking midfielder Kaká, and Ancelotti's formidable four-man back-line of Cafu, Costacurta, Alessandro Nesta and Maldini, Milan took home the UEFA Super Cup in 2003 over Porto, followed by the Scudetto in 2004 with an Italian record of 82 points from 34 games, while Shevchenko finished the season as the league's top-scorer. The Rossoneri, however, suffered penalty-shootout defeats to Juventus in the 2003 Supercoppa Italiana, and to Boca Juniors in the 2003 Intercontinental Cup. They were also knocked out by Deportivo de La Coruña in the 2003–04 UEFA Champions League.
Under Ancelotti's reign, Milan also won the 2004 Supercoppa Italiana, and were also back-to-back Serie A runners-up to Juventus in 2004–05 and 2005–06 (both Scudetti were later wiped from the record books of Juventus due to the club's involvement in the Calciopoli scandal). During the 2004–05 season, Ancelotti also led Milan to the 2005 Champions League final, where they lost out to Liverpool 2–3 on penalties after a 3–3 draw in normal time. In the Coppa Italia, the team was unable to get past the quarter finals. The following season, Milan once again faced disappointment as they lost out to Barcelona in the Champions League semi-finals, and only reached the round of 16 of the 2005–06 Coppa Italia.
After the departure of striker Andriy Shevchenko at the beginning of the 2006–07 season, Ancelotti was forced to redesign Milan's line-up once again, devising a 4–3–2–1 system that would later be known as his "Christmas Tree" formation. Milan's line-up utilised Inzaghi as a lone striker, supported by attacking midfielders Clarence Seedorf and Kaká, in front of a three-man midfield which featured Andrea Pirlo as a creative playmaker, supported by hard-working defensive midfielders Gennaro Gattuso and Massimo Ambrosini. Milan received an eight-point deduction during the 2006–07 Serie A season for their role in the Calciopoli scandal, which virtually put the team out of the title race, and instead led Ancelotti to focus on winning the Champions League. On 23 May 2007, Milan avenged their defeat to Liverpool two years earlier with a 2–1 win at the Olympic Stadium in Athens in the 2007 Champions League final, leading to Ancelotti's second Champions League trophy as Milan coach and his fourth title overall, having also won it twice as a Milan player in 1989 and 1990. During the 2006–07 season, Milan also finished fourth in Serie A, and lost out to eventual champions Roma in the Coppa Italia semi-final. The following season, Ancelotti also won the 2007 UEFA Super Cup, as well as the club's first ever FIFA Club World Cup in 2007, becoming the first manager to do so with a European side. After finishing in fifth place, Milan missed out on a Champions League spot at the end of the league season, however, and also suffered a round of 16 elimination in the Champions League, and the Coppa Italia.
In Ancelotti's final season at the club, Milan managed a third-place finish in Serie A, behind Juventus, and cross-city rivals Inter, sealing a place in the next season's Champions League, while they were eliminated in the round of 32 of the UEFA Cup, and the round of 16 of the Coppa Italia. After previously denying rumours that he would be leaving the club, Ancelotti announced his resignation from Milan less than an hour following their 2–0 victory over Fiorentina on 31 May 2009, the final match of the season. In total, Ancelotti led Milan for 423 games; only Nereo Rocco has been in charge of the club for more matches.
On 1 June 2009, Ancelotti succeeded interim manager Guus Hiddink when he was confirmed as the new Chelsea manager after agreeing to a three-year contract, and formally assumed his duties on 1 July. His salary at Chelsea was initially reported to be more than £5 million per year. Ancelotti became the club's fourth permanent manager in 21 months, following José Mourinho, Avram Grant and Luiz Felipe Scolari. He was also the third Italian to manage Chelsea, after Gianluca Vialli and Claudio Ranieri.
On 9 August 2009, Ancelotti won his first trophy as Chelsea manager, the Community Shield, beating Manchester United on penalties, following a 2–2 draw. His first Premier League game in charge of the Blues ended in a 2–1 home victory over Hull City on 15 August 2009. Chelsea lost their first match under Ancelotti at the DW Stadium away to Wigan Athletic on 26 September, losing 1–3. They were eliminated from the League Cup on 2 December, reaching the quarter-finals stage, after a penalty shootout defeat to Blackburn Rovers after a 3–3 draw at Ewood Park.
In the Champions League, Ancelotti returned to the San Siro for the first time since his departure from Milan, when his team faced Internazionale, who was at the time coached by ex-Chelsea manager José Mourinho, at the Round of 16 stage. Ancelotti and Mourinho had a tense relationship from the previous season, as managers of Milan and Inter respectively. Chelsea was eliminated from the Champions League on 16 March 2010 after a 1–3 aggregate loss to Inter, having lost 1–2 away and 0–1 at Stamford Bridge.
On 9 May 2010, Ancelotti led Chelsea to the Premier League title, beating Manchester United by one point and setting scoring records. The team finished the campaign with 103 goals, becoming the first team in the Premier League to score more than 100 goals in a season, and the first since Tottenham Hotspur in the 1962–63 season. Chelsea secured the title with an 8–0 victory over Wigan at Stamford Bridge. Ancelotti also became the first Italian manager to win the Premier League and only the fifth manager overall in the League's 18 seasons. On 15 May 2010, Ancelotti led Chelsea to victory in the 2009–10 FA Cup, beating Portsmouth 1–0 in the final at Wembley Stadium; Chelsea's third victory in the FA Cup in four years, equaling a record set by Arsenal between 2002 and 2005. The FA Cup win secured Chelsea's first ever domestic double.
The following season, after having lost to Manchester United in the 2010 FA Community Shield in August, Ancelotti led Chelsea to the top of the table on the first weekend of the season thanks to a 6–0 rout of newly promoted West Bromwich Albion. Chelsea followed up this result with another 6–0 win, this time over Wigan, while Stoke City were beaten 2–0 in the next match. Chelsea had a good start to the season, winning their first five matches. Chelsea then lost 3–4 against Newcastle United on 23 September 2010 in the League Cup. They then went on to lose against Manchester City in the Premier League 0–1 after a cleverly-taken strike by City captain Carlos Tevez. Chelsea made a good start in Europe by beating MŠK Žilina and Marseille 4–1 and 2–0, respectively, in the 2010–11 UEFA Champions League. Chelsea then defeated fourth-placed Arsenal 2–0 on 3 October 2010, courtesy of a goal from Didier Drogba and a free-kick by defender Alex.
Chelsea's next defeat of the season came against Liverpool at Anfield on 7 November 2010, where they lost 0–2 with both goals coming from Fernando Torres. A week later, Chelsea suffered their second Premier League defeat in three matches with a remarkable 0–3 home defeat to Sunderland. In their following five league games, they lost two and drew three games, culminating in a 1–3 loss to Arsenal at the Emirates Stadium. On 5 January 2011, Chelsea suffered a shock 0–1 defeat at struggling Wolverhampton Wanderers, leaving them fifth in the League and in real danger of missing out on a Champions League place for the first time since 2002. This result led to Ancelotti ruling out Chelsea's chances of retaining the title, insisting that he did not fear that he would be sacked. But after this match, however, Chelsea's form began to improve. First with a 7–0 thrashing of Ipswich Town in the FA Cup at Stamford Bridge and then a 2–0 victory over Blackburn, followed by emphatic away wins against Bolton Wanderers and Sunderland, putting them in fourth position in the league, though still ten points behind leaders Manchester United.
On 31 January 2011, Chelsea signed Liverpool striker Fernando Torres for a British record £50 million and Benfica defender David Luiz for £22 million. Chelsea lost 0–1 to Liverpool at Stamford Bridge but beat league leaders Manchester United on 1 March in a 2–1 comeback win that saw David Luiz net his first goal for Chelsea, which was followed by a 3–1 win away to Blackpool. Chelsea were later defeated by Manchester United at home and away (aggregate of 1–3) in the Champions League quarter-finals.
Following their defeat in the Champions League, Chelsea made a remarkable comeback in the league, defeating Wigan 1–0 at home, West Brom 3–1 away, Birmingham City 3–1, West Ham United 3–0 and Tottenham 2–1 at home. Chelsea, who at one point were fifth and 15 points behind leaders Manchester United, vaulted into the second position the league, just three points behind them with three games left of the season.
On 8 May, however, Chelsea lost 1–2 against Manchester United at Old Trafford to stay second in the league, now six points behind the leaders with just two more games to play.
Ancelotti was sacked less than two hours after a 0–1 away defeat against Everton on 22 May 2011, Chelsea's last Premier League match of the season. They had finished the 2010–11 Premier League in second place. He was earning £6.5 million per year at Chelsea just before his departure from the club. He reportedly received a severance payment of £6 million from Chelsea. Ancelotti finished with a record of 67 wins, 20 draws and 22 losses in 109 matches. Ancelotti's win percentage at Chelsea is the third-highest in Premier League history, behind only José Mourinho and Sir Alex Ferguson.
On 30 December 2011, with Paris Saint-Germain at the top of the Ligue 1 with three points down to Montpellier, Ancelotti was appointed as the new manager of the club on the same day as their previous manager, Antoine Kombouaré, was released from his contract. His salary at PSG was reported to be €6 million per year. On 21 March 2012, Ancelotti experienced his first defeat in charge of PSG as the club fell to a 1–3 defeat at the hands of Lyon in a Coupe de France quarter-final match. Ten days later, PSG suffered their first Ligue 1 defeat under Ancelotti when they lost 1–2 away to Nancy. PSG ended up as runners-up in Ligue 1 in Ancelotti's first season in charge, three points behind winners Montpellier. He also took PSG to the Coupe de France quarter-finals. The club were eliminated from the Coupe de la Ligue and UEFA Europa League prior to Ancelotti's appointment.
During Ancelotti's first full season at the club, PSG entered the winter break at the top of the Ligue 1 table ahead of Lyon and Marseille on goal difference. They clinched the Ligue 1 title on 12 May 2013 with two matches to spare. The club reached the quarter-final of the Champions League, where they lost to Barcelona on the away goals rule (3–3 on aggregate), the quarter–final of the Coupe de France and the quarter–final of the Coupe de la Ligue. On 19 May 2013, Ancelotti asked to leave the club, then joined Real Madrid.
On 25 June 2013, Ancelotti became the manager of Real Madrid as the replacement for the departing José Mourinho, signing a three-year deal. He was introduced at a press conference at the Santiago Bernabéu Stadium, where it was also announced that Zinedine Zidane and Paul Clement would be his assistant coaches. Shortly following his arrival, Real Madrid confirmed the signing of Isco for a fee of €24 million which was followed by the signing of Asier Illarramendi for €32 million. Argentinean striker Gonzalo Higuaín left the club for €40 million to Napoli. This, along with the sale of Mesut Özil to Arsenal, paved way for new world record signing Gareth Bale for £86 million (€105M) from Tottenham Hotspur. In Ancelotti's first league game in charge, on 18 August 2013, Real Madrid won 2–1 at home against Real Betis. At Real Madrid, Ancelotti eventually deviated from the 4–2–3–1 formation which had been deployed by his predecessor, switching instead to a 4–3–3 formation to great effect, in which Argentine winger Ángel Di María particularly excelled as a left-sided central midfielder, and played a key role in the club's successes. On 16 April 2014, Ancelotti won his first major trophy as Real Madrid manager after they defeated Barcelona 2–1 in the Copa del Rey final held at the Mestalla Stadium. On 29 April, Real Madrid defeated Bayern Munich in the semi-finals of the Champions League by an aggregate score of 5–0 (1–0 in Madrid and 0–4 in Munich), with Los Blancos reaching their first final since they last won the competition in 2002. On 24 May, Real Madrid won their tenth Champions League trophy after defeating Atlético Madrid in the final 4–1 in extra time. He became only the second manager after Liverpool's Bob Paisley to win the competition on three occasions and the first man to win the Champions League/European Cup twice as a player and three times as a manager to this day. In addition to winning Champions League, they finished third in La Liga, losing the tiebreaker for second place against Barcelona, and winning Copa del Rey.
On 12 August, Ancelotti's team won another European trophy, leading Real Madrid to a 2–0 victory over Sevilla in the 2014 UEFA Super Cup. In the last four months of 2014, his team set a Spanish record of 22 consecutive match victories in all competitions that began on 16 September and culminated with Real Madrid's first FIFA Club World Cup title in December 2014, finishing the year 2014 with four trophies. By securing only a third-place finish for the 2013–14 La Liga season, he became the first Real Madrid manager to finish outside the top two of La Liga since the 2003–04 season, and also the first Real Madrid manager to finish behind city rivals Atlético since the 1995–96 season. On 1 December 2014, Ancelotti was nominated as one of the three finalists for the 2014 FIFA World Coach of the Year Award. On 19 January 2015, Ancelotti was inducted into the Italian Football Hall of Fame and on 20 January 2015, he won the IFFHS 2014 Award as The World's Best Club Coach. Real Madrid finished the 2014–15 league season in second place, scoring 118 goals in the process. They were eliminated in the round of 16 in the Copa del Rey. On 25 May 2015, Real Madrid president Florentino Pérez announced that the club's board had taken "a very difficult decision" to relieve Ancelotti of his duties with immediate effect. Pérez stated that Ancelotti had won the hearts of both the board and fans, and would always have a place in the club's history because he was the coach that led them to the Décima. "However at this club the demands are huge and we need a new impulse in order to win trophies and be at our best," he added.
After leaving Madrid, Ancelotti held talks about a return to Milan, which he rejected, saying, "It was hard to say no to such a beloved club to me, but I need some rest. I wish them the best." He stated that he wanted to take a year off and undergo an operation for his spinal stenosis. He later relocated to Vancouver, British Columbia, Canada.
On 20 December 2015, Bayern Munich CEO Karl-Heinz Rummenigge confirmed that Ancelotti would replace Pep Guardiola as manager for the 2016–17 season, signing a three-year contract. His contract started on 1 July 2016. His first training session was on 11 July 2016 and his first match was a pre–season win against SV Lippstadt 08. His first match at Allianz Arena was a 1–0 pre–season win over Manchester City. Bayern participated in the International Champions Cup. In the first match, Bayern lost to Milan in a shootout. In the second match, Bayern defeated Inter Milan. In the final match, Bayern lost to Real Madrid. On 14 August 2016, Bayern defeated Borussia Dortmund 2–0 in the German Super Cup. This was his first trophy as Bayern's manager. On 26 August 2016, in his Bundesliga debut, Bayern defeated Werder Bremen 6–0. In addition to defeating Borussia Dortmund, Carl Zeiss Jena, and Werder Bremen, they defeated Schalke 04, Rostov, Ingolstadt 04, Hertha BSC, and Hamburger SV to win his first eight matches as head coach before losing to Atlético Madrid. They continued their winless streak against 1. FC Köln and Eintracht Frankfurt before defeating PSV Eindhoven. After the win against Eindhoven, Bayern went on a three match winless streak. Bayern drew against 1899 Hoffenheim and lost against Borussia Dortmund and Rostov before defeating Bayer Leverkusen. On 29 April, Ancelotti led Bayern to their fifth consecutive Bundesliga title and their 27th overall following a 6–0 away win over Wolfsburg. However, Bayern were eliminated in the Champions League in a controversial quarter-final clash against Ancelotti's former team Real Madrid. They also lost 3–2 to Borussia Dortmund in the DFB-Pokal semi-finals.
Towards the beginning of his coaching career, and during his time with Parma, Ancelotti preferred to use a rigorous 4–4–2 formation, which made use of heavy pressing, and drew influence from that of his Milan and Italy coach Arrigo Sacchi, and which he believed to be the most successful system for his team; however, this system did not allow for more creative forwards, such as Gianfranco Zola, Hristo Stoichkov, and Roberto Baggio, to play in their preferred positions, and ultimately led to the Zola and Stoichkov's departure from the club, while Baggio's transfer to Parma in 1997 was impeded by Ancelotti. Ancelotti later stated that he regretted his intransigence, and when he joined Juventus, he abandoned his favoured 4–4–2 in order to accommodate Zinedine Zidane in his preferred advanced playmaking role behind the forwards. In addition to Sacchi, Ancelotti has also cited his former Roma manager Nils Niedholm, and his youth coach Bruno Mora as major influences.
Despite his initial reputation as a tactically inflexible coach, with Milan Ancelotti later drew praise for his ability to find systems which would best suit his players, and which allowed several talented and creative players to co-exist; under Ancelotti's management, the club enjoyed one of its most fruitful spells in its history. Carlo Ancelotti's Milan sides usually almost always used a strong four-man back-line, a main striker and an attacking midfielder. In his first seasons with the club, although he was initially criticised by the club's president Berlusconi, due to his supposedly defensive tactics, Ancelotti was able to implement a more creative playing style based on possession when he notably adopted a 4–3–1–2, 4–1–2–1–2 or 4–4–2 diamond formation. While still preserving the team's strong defensive line, Ancelotti converted attacking midfielder Andrea Pirlo to a deep-lying playmaker, which saw him play in a seemingly defensive midfield role in front of the back-line, and behind the team's advanced playmaker, either Rui Costa or Rivaldo, giving the Italian more time on the ball to orchestrate the team's attacking moves from deeper areas, or to create goalscoring opportunities for the team's prolific strikers with his accurate long passing ability; the team's two playmakers were supported defensively by box-to-box midfielders on either side of them in the midfield diamond. Due to competition from Alessandro Nesta, Paolo Maldini, Roque Júnior, Dario Šimić, and later Jaap Stam in defence, he also converted former centre-back Alessandro Costacurta to a defensive left-back, alternating him with Kakha Kaladze or Giuseppe Pancaro, while, due to the club's narrow midfield, the club's attacking right-back, Cafu, was given license to attack and provide width to the team; due to Cafu's offensive capabilities, Ancelotti occasionally fielded a 4–4–1–1 or 3–4–1–2 formation, which saw Cafu used as an outright winger, along with Serginho or Marek Jankulovski on the left. After the departure of one of the club's main strikers at the beginning of the 2006–07 season, Andriy Shevchenko, Ancelotti redesigned Milan's line-up, devising a 4–3–2–1 system, later known as his "Christmas Tree" formation. Milan's line-up utilised either Filippo Inzaghi or Alberto Gilardino as a lone striker, supported by two attacking midfielders, Clarence Seedorf and Kaká, in front of a three-man midfield which once again featured Andrea Pirlo as a deep-lying playmaker, supported by two hard-working defensive midfielders, such as Gennaro Gattuso, Massimo Ambrosini, or Cristian Brocchi.
At Real Madrid, Ancelotti similarly drew praise for his versatility; he modified the team's 4–2–3–1 formation, which had been used under José Mourinho, to a 4–4–2 formation, before settling on a 4–3–3 formation, in which Argentine former winger Ángel Di María was converted to a left-sided central midfielder, while Cristiano Ronaldo was played in his preferred free role on the left wing. Di María particularly excelled in thie new role and played a key role in the club's successes.
In addition to his tactical prowess and adaptability, Ancelotti has also drawn praise for his kindness, good humour, and his calm, balanced approach as a manager, as well as for his ability to motive and cultivate a good relationship with his players, and foster a united, winning team environment, although he has also been known to lose his temper at times. During Ancelotti's first season with Bayern Munich, Spanish midfielder Thiago praised Ancelotti for the freedom he gave the players to express themselves and for the confidence with which he instilled them; Ancelotti commented on the tactical changes he implemented at Bayern Munich, stating "[t]he main change is we press a bit more intermittently and we try to play more directly, more vertically," also adding that "if you're organised even an ordinary player can do very well because he'll have options and he'll know where they are and how to find them. But when you get to the final third, everything changes. That's where you need creativity and freedom because without it you only have sterile possession. Especially if your opponent's defence is organised and has been paying attention."
Ancelotti has two children: a daughter, Katia; and a son, Davide, who also played in the Milan youth team and later joined Borgomanero in June 2008. In 2008, Ancelotti confirmed in an interview that he had broken up with his wife of 25 years, Luisa Gibellini. Then he dated Marina Cretu. In 2011, it was announced he was dating Canadian businesswoman Mariann Barrena McClay. Ancelotti and Barrena McClay married in Vancouver in July 2014.
In May 2009, Ancelotti's autobiography, Preferisco la Coppa ("I Prefer the Cup", with a word-play by Ancelotti on the Italian word "coppa" that stands both for "cup" and a type of cured cold pork meat cut, which is produced in Ancelotti's native region of Emilia-Romagna), was published, with all proceeds from sales of the book going to the Fondazione Stefano Borgonovo for the funding of research on amyotrophic lateral sclerosis.
In his last season with Chelsea, Ancelotti had to travel back to Italy on a regular basis to visit his 87-year-old father who was in poor health with diabetes and other issues. On the issue, he said, "I don't have a problem managing the team for this reason. It's difficult, emotionally, when it's your father... but this is life. I have to do my best to stay close to him, but this is the life." His father died on 29 September 2010, aged 87.As of 16 September 2017
Serie A: 1982–83
Coppa Italia: 1979–80, 1980–81, 1983–84, 1985–86
European Cup: 1988–89, 1989–90
UEFA Super Cup: 1990
Serie A: 1987–88, 1991–92
Supercoppa Italiana: 1988
Intercontinental Cup: 1989
FIFA World Cup Bronze Medal: 1990
UEFA Intertoto Cup: 1999
Serie A: 2003–04
Coppa Italia: 2002–03
Supercoppa Italiana: 2004
UEFA Champions League: 2002–03, 2006–07
UEFA Super Cup: 2003, 2007
FIFA Club World Cup: 2007
Premier League: 2009–10
FA Cup: 2009–10
FA Community Shield: 2009
Ligue 1: 2012–13
Copa del Rey: 2013–14
UEFA Champions League: 2013–14
UEFA Super Cup: 2014
FIFA Club World Cup: 2014
DFL-Supercup: 2016, 2017
Serie A Coach of the Year: 2001, 2004
Panchina d'Oro: 2002–03, 2003–04
Ligue 1 Manager of the Year: 2012–13 (tie with Christophe Galtier)
IFFHS World's Best Club Coach: 2007, 2014
European Coach of the Year—Alf Ramsey Award: 2003
World Soccer Magazine Manager of the Year: 2003
Globe Soccer Awards Best Coach of the Year: 2014
Globe Soccer Awards Best Media Attraction in Football: 2014
Enzo Bearzot Award: 2014
FIFA World Coach of the Year (Runner-up): 2014
Miguel Muñoz Trophy: 2014–15
Italian Football Hall of Fame: 2015
A.C. Milan Hall of Fame
A.S. Roma Hall of Fame
5th Class/Knight: Cavaliere Ordine al Merito della Repubblica Italiana
5th Class/Officer: Ufficiale dell'Ordine della Stella d'Italia