He began his career at Cesena, and after loans at three lower-league clubs, helped them to consecutive promotions to reach Serie A. He then left to Juventus, where he won the league title in both of his seasons. He joined Sunderland on a four-year deal in 2013, before moving to Napoli in 2016.
Giaccherini has earned over 20 caps for the Italy national football team, helping the nation to the final of UEFA Euro 2012 and a third-place finish at the 2013 FIFA Confederations Cup, also taking part at UEFA Euro 2016.
Born in Bibbiena, Tuscany, Giaccherini started his professional career at Romagna team Cesena. He scored 15 goals in the group stages of the Campionato Nazionale Primavera in the 2003–04 season. He was then sent out on loan to Lega Pro clubs Forli, Bellaria Igea and Pavia for 4 seasons.
Cesena was relegated to the Lega Pro Prima Divisione in 2008, when Giaccherini returned and was partnered with Simone Motta in attack. Cesena came top of the Prima Divisione in June 2009. Due to their good defensive record Cesena finished as runner-up in the 2009–10 Serie B season and was therefore promoted to Serie A, where Giaccherini was partnered with Guilherme do Prado, Dominique Malonga, Ezequiel Schelotto and Cristian Bucchi in attack, none of whom managed to hit double figures.
In August 2010 Cesena offered a new contract to Giaccherini as his current contract was due to expire in 2012.
In the 2010–11 Serie A season Giaccherini remained a first-choice starter and was partnered with wing-forward Schelotto and Erjon Bogdani. The club once again reached the top of the table but went on a winless run after the third match as a result of which Luis Jiménez replaced Schelotto as Giaccherini's new attacking partner. Giaccherini managed to score in 7 matches that season, including a goal in a 2–0 win against Milan and once in a 2–3 lose to Inter. He also scored a brace on 6 March as Cesena beat Sampdoria 3–2, and managed 3 more goals in the last 7 matches of the season.
He made 4 assists in his maiden Serie A season which was one short of Luca Ceccarelli.
On 25 August 2011, Giaccherini officially transferred to Juventus on a €3 million co-ownership with Cesena retaining 50% of his contract. He made his competitive debut for Juventus against Parma. On 8 December 2011, he scored his first goal for the Bianconeri, an angled solo effort in a 2–1 win over Bologna in the Coppa Italia. He scored his first Serie A goal for the club on 21 January 2012, scoring the second in a 2–0 victory over Atalanta on a volley from Luca Marrone. Three days later he scored the first goal in Juventus's 3–0 Coppa Italia victory against Roma. Due to injuries and suspensions to first choice centre midfielders Claudio Marchisio and Arturo Vidal, Conte has played him in a more central role. Juventus won the Serie A title unbeaten that season and reached the final of the Coppa Italia, losing to Napoli.
In June 2012 Juventus bought him outright for €4.25 million, in a deal that would keep him tied to the club until June 2015. Juventus won the Supercoppa Italiana against Napoli and retained the Serie A title during the 2012–13 season. They also reached the semi-finals of the Coppa Italia and the Quarter-finals of the UEFA Champions League, losing, in both competitions, to the respective winners, Lazio and Bayern Munich.
On 11 July 2013, Juventus manager Antonio Conte confirmed the sale of Giaccherini to English club Sunderland, in order to raise funds.
Sunderland confirmed the signing of Giaccherini on 16 July 2013, on a four-year contract after joining up with his new team during their pre-season training camp near Lake Garda.
He made his debut on 17 August, in a 1–0 defeat at home to Fulham. In his second match of the campaign, he scored a headed goal as Sunderland drew 1–1 away to Southampton on 24 August. His first cup goal came on 24 September 2013 in a 2–0 League Cup win against Peterborough. His second league goal, came in the following game at home to Liverpool, on 29 September 2013. He was the first to react as Simon Mignolet spilled a Ki Sung-yueng shot, and finished from six yards. On 22 February 2014 Giaccherini scored his fourth goal from a 25-yard shot in a 4–1 loss against Arsenal.
Giaccherini appeared as a 77th-minute substitute for Lee Cattermole in the League Cup Final on 2 March, but was unable to prevent Sunderland losing 3–1 to Manchester City. On 17 April, Giaccherini came on as a substitute with Sunderland trailing 1–0 in the league at the City of Manchester Stadium, and assisted both of Connor Wickham's goals as Sunderland went on to draw 2–2. He scored his fifth goal of the season, and fourth in the league, on 27 April 2014, when he scored the third goal in Sunderland's 4–0 win against Cardiff City, a result which saw Sunderland move out of the relegation zone.
Giaccherini chose to remain at Sunderland for the 2014–15 season, despite missing out on a place in Italy's squad at the 2014 FIFA World Cup. However, he suffered an injury in a pre-season match with Real Betis which ruled him out of the start of the season. He then suffered an ankle injury in a 0–0 draw at Burnley in September, ruling him out for several more weeks. After suffering another ankle injury in February in a 3–1 FA Cup win at Fulham, Giaccherini was ruled out for the rest of the season. On 24 May 2015, Giaccherini made his comeback on the last day of the season when he came off the bench for the last fifteen minutes in a 1–3 away defeat to Chelsea.
On 31 August 2015, Giaccherini returned to Italy, joining newly promoted Serie A side Bologna on a season long-loan. He suffered yet another injury on 14 September, in a 2–0 away league defeat to Sampdoria, on his debut with the club.
On 16 July 2016, Giaccherini joined Napoli for a reported €1.5 million fee plus bonuses.
Giaccherini was included in Cesare Prandelli's 23-man squad for UEFA Euro 2012. He won his first cap for Italy starting as a left wing-back in a 3–5–2 formation against World Cup champions and defending European Champions Spain on 10 June. Italy eventually reached the final of the tournament, facing Spain once again, and suffering a 4–0 defeat.
Giaccherini opened the scoring after only 19 seconds of Italy's pre-Confederations Cup friendly against Haiti in Rio de Janeiro on 11 June 2013, played to raise funds for victims of the 2010 Haiti earthquake. The goal was the fastest in Italy's history, one second quicker than Salvatore Bagni's goal against Mexico in 1984.
Giaccherini was included in the 23-man Italy squad for the 2013 FIFA Confederations Cup in Brazil. Giaccherini played in every match of the tournament and was one of Italy's most important players throughout the competition; in the opening game against Mexico on 16 June, he assisted Mario Balotelli's match-winning goal. In Italy's second match against Japan, a pass across goal by Giaccherini was deflected by Atsuto Uchida, who scored an own goal; the match ended 4–3 to Italy, qualifying them for the semifinals of the tournament for the first time in their history. Giaccherini scored Italy's temporary equaliser against hosts Brazil in the final group match, although they eventually lost the match 4–2.
He started in the semifinal against Spain, which ended in a 0–0 draw, although Giaccherini hit the post in extra time. Spain went through to the final after winning the resulting shootout 7–6. Italy managed to win the bronze medal match 3–2 on penalties against Uruguay, after a 2–2 draw following extra time, with Giaccherini netting Italy's last penalty before Gianluigi Buffon won the match for Italy by saving Walter Gargano's spot kick. Due to his exploits throughout the tournament, the Brazilian fans gave him the nickname Giaccherinho.
On 31 May 2016, Giaccherini was named to Antonio Conte's 23-man Italy squad for UEFA Euro 2016. On 13 June 2016, in Italy's first match of Euro 2016, Giaccherini slotted a goal after a half-pitch pass from Leonardo Bonucci to take the lead against Belgium in an eventual 2–0 victory. He was later named man of the match. In the round of 16 at Stade de France in Paris on 27 June, he assisted Giorgio Chiellini's opening goal in a 2–0 win over defending champions Spain. On 2 July, he converted a penalty in a 6–5 shoot-out defeat to defending World Cup champions Germany in the quarter-finals of the competition.
Giaccherini is a consistent, energetic, quick, hard-working, and versatile player. He is capable of aiding his team defensively, but also offensively, due to his ability to make attacking runs, contributing with goals, and assists, due to his reliable distribution. A technically gifted player, he was initially deployed as a winger on either flank early in his career, due to his dribbling ability, agility, acceleration, and balance, which aid him in beating players in one on one situations. He is capable of playing anywhere in midfield, however, and has more recently been deployed as a central midfielder, as a wing-back, or as an attacking midfielder.As of 3 June 2016
1Includes Coppa Italia, Coppa Italia Serie C, Coppa Italia Lega Pro, Football League Cup and FA Cup.
2Includes UEFA Champions League.
3Includes Supercoppa Italiana.As of 2 July 2016.
As of match played 13 June 2016.
Scores and results list Italy's goal tally first.
Serie A: (2) 2011–12, 2012–13
Supercoppa Italiana (1) 2012
Coppa Italia: Runner-up 2011–12
Football League Cup: Runner-up 2013–14
UEFA European Championship: Runner-up 2012
FIFA Confederations Cup: Third Place 2013