The knockout phase of the 2008–09 UEFA Champions League began on 24 February 2009 and concluded with the final at the Stadio Olimpico in Rome on 27 May 2009. The knockout phase involves the 16 teams who finished in the top two in each of their groups in the group stage.
Each tie in the knockout phase, apart from the final, will be played over two legs, with each team playing one leg at home. The team that has the higher aggregate score over the two legs will progress to the next round. In the event that aggregate scores finish level, the team that scored more goals away from home over the two legs will progress. If away goals are also equal, 30 minutes of extra time are played. If there are goals scored during extra time and the aggregate score is still level, the visiting team qualifies by virtue of more away goals scored. If no goals are scored during extra time, there will be a penalty shootout after extra time.
In the draw for the first knockout round, matches are played between the winner of one group and the runner-up of a different group. The only restriction on the drawing of teams in the first knockout round is that the teams must not be from the same national association or have played in the same group in the group stages. From the quarter-finals onwards, these restrictions do not apply.
In the final, the tie is played over just one leg at a neutral venue. If scores are level at the end of normal time in the final, extra time is played, followed by penalties if scores remain tied.
The draw for the first knockout round of the 2008–09 UEFA Champions League was held on 19 December 2008, and conducted by UEFA General Secretary David Taylor and Bruno Conti, the ambassador for the 2009 UEFA Champions League Final. The first legs of the first knockout round were played on 24 and 25 February 2009, while the second legs were played on 10 and 11 March.
The knockout phase began on 24 February with four first-leg ties. English side Arsenal gained a first leg advantage with a 1–0 home victory against Roma at the Emirates Stadium, courtesy of Robin van Persie's 37th-minute penalty. The other English team in action, Manchester United, drew 0–0 with Internazionale at the San Siro, failing to score the away goal they had been hoping for. The other two matches finished in score draws, with the away sides having the upper hand going into the second legs. Lyon drew 1–1 with Barcelona at the Stade de Gerland in France, with Barcelona's Thierry Henry cancelling out an opener from Juninho. Porto came from behind twice away to Atlético Madrid to secure a 2–2 draw at the Vicente Calderón Stadium. Maxi Rodríguez put Atlético in front in the fourth minute, Lisandro López equalised in the 22nd minute, Diego Forlán scored on the stroke of half-time to restore Atlético's advantage but López levelled in the 72nd minute.
In the second set of first leg ties, played on 25 February 2009, three teams scored away goals. Bayern Munich scored five times without reply away to Sporting CP. In the match at the Estádio José Alvalade, Franck Ribéry gave the Germans the lead in the 42nd minute and Miroslav Klose doubled their advantage in the 57th. Ribéry scored again from the penalty spot in the 63rd before a brace from Luca Toni put the tie out of Sporting's reach, even before the second leg. Five-time winners Liverpool also managed an away win, against nine-time winners Real Madrid, but had to wait until the 82nd minute at the Santiago Bernabéu Stadium for it, when Yossi Benayoun scored a header from Fábio Aurélio's free-kick to hand them the advantage for the second leg. Villarreal and Panathinaikos shared a score draw at the Estadio El Madrigal, with Giuseppe Rossi scoring a 67th-minute penalty to cancel out Giorgos Karagounis' 59th-minute opener. In the other game, Chelsea beat Juventus at Stamford Bridge courtesy of a 12th-minute strike from Didier Drogba.
All times are Central European Time (UTC+1)
In the four second leg ties played on 10 March, the two English clubs in action both progressed along with Bayern Munich and Villarreal. Liverpool eliminated the nine-time European Cup winners Real Madrid with a 4–0 home victory. Fernando Torres doubled Liverpool's aggregate lead in the 16th minute, and Steven Gerrard made it 2–0 on the night with a 28th-minute penalty. Gerrard further extended Liverpool's lead two minutes after half-time and Andrea Dossena made it 5–0 on aggregate with two minutes left. Chelsea also made it through to the quarter-finals with a 2–2 draw, having won the first leg at Stamford Bridge 1–0. They fell behind to a goal from Vincenzo Iaquinta in the 19th minute but equalised through Michael Essien on the stroke of half-time. Juventus went back in front through an Alessandro Del Piero penalty, although Chelsea were heading through on the away goals ruling. Chelsea sealed their passage to the last eight when Didier Drogba equalised in the 83rd minute to win 3–2 on aggregate.
In the other games, Sporting CP departed the competition after setting a new Champions League record aggregate defeat of 12–1 to Bayern Munich. An early goal from Lukas Podolski extended Bayern's lead to 6–0 on aggregate and this was followed up by further strikes before half-time from Podolski again, Ânderson Polga and Bastian Schweinsteiger, sandwiched by a consolation from Sporting's João Moutinho. Bayern were not finished at 4–1 as Mark van Bommel, Miroslav Klose and Thomas Müller further added to the scoreline. Villarreal were the fourth side to make it into the quarter-finals by beating Panathinaikos 3–2 overall. Ariel Ibagaza put Villarreal 2–1 up on aggregate in the 49th minute, Evangelos Mantzios equalised six minutes later, but Joseba Llorente turned the tie in Villarreal's favour in the 70th minute and the match finished 2–1 to Villarreal.
The remaining two English sides both reached the quarter-finals on 11 March and they were joined by Porto and Barcelona. Manchester United defeated Internazionale 2–0 on aggregate at Old Trafford. After a 0–0 draw at the San Siro in the first leg, United were aware that an away goal for Inter would make it difficult, but they made the perfect start with centre back Nemanja Vidić scoring with a header after four minutes. Cristiano Ronaldo doubled the lead just after half-time and the match finished 2–0. Porto and Atlético Madrid played out a 0–0 draw at the Estádio do Dragão in Portugal, but Porto went through on the away goals rule, having scored twice in a 2–2 draw in Spain. Barcelona beat Lyon 6–3 on aggregate with a 5–2 win at the Camp Nou. Thierry Henry scored twice in the space of a couple of minutes shortly before the half-hour mark to put Barcelona 3–1 up on aggregate before Lionel Messi and Samuel Eto'o made it 4–0 just before half-time on the night. Lyon scored two consolation goals through Jean Makoun on the stoke of half-time and Juninho just after the break, but Barcelona added a fifth in the final minute. In the last game to finish, Roma defeated Arsenal 1–0 at the Stadio Olimpico with Juan scoring in the ninth minute. The first match had finished 1–0 to Arsenal so the match headed into extra-time and, eventually, penalties. Arsenal emerged victorious in the shootout, winning 7–6 after Max Tonetto missed Roma's final spotkick.
Villarreal won 3–2 on aggregate.
Liverpool won 5–0 on aggregate.
Bayern Munich won 12–1 on aggregate.
Chelsea won 3–2 on aggregate.
Atlético Madrid 2–2 Porto on aggregate. Porto won on away goals.
Barcelona won 6–3 on aggregate.
Arsenal 1–1 Roma on aggregate. Arsenal won 7–6 on penalties.
Manchester United won 2–0 on aggregate.
The draw for the quarter-finals of the competition took place in Nyon, Switzerland, on 20 March 2009. There was no seeding and no country protection, meaning that it was an entirely random draw. The first legs were played on 7/8 April while the second legs were played on 14/15 April. Liverpool requested that their second leg be played on 14 April so that it avoid a clash with the 20th anniversary of the Hillsborough Disaster on 15 April.
All times are Central European Summer Time (UTC+2)
English sides Manchester United and Arsenal were involved in the first two quarter-final matches on 7 April. Arsenal were playing the first leg away against Villarreal from Spain, their second encounter in three years following on from a meeting in the semi-finals three years earlier. Villarreal went in front in the 10th minute thanks to a long-range effort from Marcos Senna. The Yellow Submarine went on to dominate the first half, but Arsenal did not concede again and their defensive work was rewarded in the 66th minute as a clipped ball from Arsenal captain Cesc Fàbregas was controlled on the chest by Emmanuel Adebayor and volleyed acrobatically with an overhead kick into the bottom corner. The match eventually finished 1–1, with Arsenal taking an away goal into the second leg.
Manchester United played their first leg at home at Old Trafford against Porto, the team who had knocked them out in the first knockout round five years before. Porto took an early lead, in the fourth minute, when Cristian Rodríguez netted past Edwin van der Sar. The advantage lasted only 11 minutes, however, at which point Wayne Rooney scored the equaliser, chipping the ball over the advancing Helton following a careless back-pass from Bruno Alves. In an open game, in which Porto dominated, another goal appeared certain but did not come until the 85th minute. Carlos Tevez saw off his marker to score from a Rooney flick from a couple of yards out. The action had not finished however and Mariano González equalised in the final minute to hand Porto a second away goal.
Liverpool and Chelsea faced each other in an all-English tie at Anfield on 8 April. The sides were meeting in the Champions League for the fifth straight season, having last faced each other in the competition in the 2008 semi-final, when Chelsea advanced to the final. Fernando Torres handed an early advantage to Liverpool, scoring in the sixth minute. However, their lead only lasted until the 39th minute when the Liverpool defence allowed Branislav Ivanović too much space at a corner and he was able to power a header past Pepe Reina. Chelsea took the lead in the 62nd minute from an almost identical situation as Ivanović scored his second headed goal. Didier Drogba added a final goal to make it 3–1 to the away side with a side-footed finish.
In the final game, played on the same evening, two of the most successful European clubs, Barcelona and Bayern Munich met at the Camp Nou in Spain. It was their first meeting since the group stage of the 1998–99 tournament. Bayern had beaten Sporting CP 12–1 in the previous round, but Barcelona posed a far tougher proposition and it showed. Lionel Messi put Barcelona in front in the ninth minute and Samuel Eto'o doubled the lead three minutes later. Messi scored his second goal in the 38th minute and Thierry Henry made it 4–0 in the 43rd minute. The score remained at 4–0 throughout the second half, leaving Barcelona as favourites to progress.
In the first two of four second-leg ties, Chelsea came with a 3–1 advantage over Liverpool and the bonus of three away goals, Liverpool came into their match knowing they needed to score three times without conceding to progress, or win 3–1 to take the game to extra time at Stamford Bridge. Despite starting the match as outsiders, Liverpool looked to be well on the way towards their target as they took a 2–0 lead within half an hour and levelled the scores at 3–3 on aggregate. Fábio Aurélio scored directly with a free kick from the left of the penalty area in the 19th minute to hand them the lead and this was doubled nine minutes later from the penalty spot: Xabi Alonso stepped up to score following a foul on him by Branislav Ivanović. But six minutes after half-time, Didier Drogba made the score 2–1 with a shot that went through the hands of Pepe Reina, and six minutes later, Chelsea equalised to 2–2 when Alex scored with a powerful free kick. Frank Lampard put Chelsea 3–2 up in the 76th minute and, at this stage, Liverpool needed to score three goals to advance. Goals from Lucas and Dirk Kuyt in the 81st and 83rd minutes, respectively, put Liverpool 4–3 up on the night and only a goal away from advancing. However, Lampard scored again in the 89th minute to finish the tie off, and the match ended 4–4 and 7–5 to Chelsea overall.
In the other match to take place that evening, Barcelona and Bayern Munich played out a 1–1 draw at the Allianz Arena. Bayern trailed the tie 4–0 following the first match at the Camp Nou and they were able to play without fear in the first half. Luca Toni and Franck Ribéry created chances in the first half but Barcelona weathered the storm and created their only meaningful chance of the first half through Dani Alves. They managed to pull a goal back early in the second half, when Zé Roberto took the ball past defender Yaya Touré and set up Ribéry who was able to score past Víctor Valdés. But Barcelona put the tie beyond the reach of Bayern with an equaliser from Seydou Keita at the end of a 17-pass move. The match finished 1–1, giving Barcelona a 5–1 aggregate win to set up a fourth tie with Chelsea in five seasons two weeks later.
The third second-leg tie was finely poised at 1–1 between Arsenal and Villarreal at the Emirates Stadium, with Arsenal ahead courtesy of the away goals rule; Villarreal came into the match knowing they had to score. Both teams were without key players: Arsenal had to play without goalkeeper Manuel Almunia, William Gallas and Gaël Clichy while captain Marcos Senna and Santi Cazorla were missing for Villarreal. Theo Walcott delivered some dangerous crosses and Robin van Persie missed an early chance from Samir Nasri's cross, but Diego Godín also tested Arsenal goalkeeper Łukasz Fabiański with a volley. Arsenal, however, took the lead in the 10th minute as Walcott raced onto a Fàbregas through-ball and chipped the ball over Diego López. Villarreal continued to create chances, including Robert Pirès nearly marking his return to his former club with a goal. Emmanuel Adebayor followed up a Van Persie free kick with a header on goal, but Gonzalo Rodríguez cleared the ball off the line. After half-time, Van Persie had a shot from distance charged down, but Arsenal did score a second goal in the 60th minute as Van Persie opted to slide a pass through to Adebayor, and his strike partner applied the finish. The tie was over in the 69th minute when Godín was adjudged to have fouled Walcott; Sebastián Eguren collected a second yellow card for his protests before Van Persie scored from the penalty spot. The match finished 3–0 to Arsenal, with Arsenal winning 4–1 on aggregate.
The final quarter-final second leg tie was between Porto and Manchester United, played simultaneously with Arsenal's match. Porto had the advantage of two away goals, after drawing 2–2 at Old Trafford. Manchester United looked to recall Rio Ferdinand from a back injury to partner Nemanja Vidić in central defence. Despite a mixed season, Cristiano Ronaldo had still scored 20 goals in all competitions and won numerous awards and he added his 21st goal with a 35-metre strike after only six minutes. Porto created very few chances, their only meaningful shot being a free kick that went wide of Edwin van der Sar's goal in the first half and later a chance for Lisandro López. United played the game at a controlled pace, but they were unable to score a second goal to settle the nerves – the threat remained that if Porto scored late, United would be knocked out. Ronaldo had a shot saved by the Porto goalkeeper Helton and Vidić missed from a couple of yards. They held on to become the first English team to win at Porto and keep their ambition of winning five trophies in the same season alive. It was United's first clean sheet in six matches and set up a semi-final with fellow English team Arsenal.
Chelsea won 7–5 on aggregate.
Barcelona won 5–1 on aggregate.
Arsenal won 4–1 on aggregate.
Manchester United won 3–2 on aggregate.
The draw for the semi-finals took place immediately after the draw for the quarter-finals. The first legs were played on 28/29 April and the second legs on 5/6 May.
Although Chelsea had achieved a goalless draw at the Camp Nou, Barcelona went into the game as favourites. The game started well for Chelsea and after nine minutes Michael Essien scored a 20-yard left-footed volley after Barcelona failed to clear a pass into the box from Frank Lampard. The first half came to a close with Chelsea leading 1–0. Despite Barcelona dominating possession, Chelsea continued to be the most dangerous side, especially following the sending off of Éric Abidal, with Chelsea also calling for up to four penalties, none of them being awarded by Norwegian referee Tom Henning Øvrebø. A 93rd-minute equaliser from a shot by Andrés Iniesta – which happened to be Barcelona's only shot on target – allowed Barcelona to ensure a last-minute qualification to the final.
Almost as soon as referee Øvrebø blew the final whistle, several Chelsea players surrounded him with complaints regarding his decisions. Some players, like Frank Lampard and Iniesta, respectfully swapped shirts, while others, such as Michael Ballack and Didier Drogba, continued to shout at the referee and contest him, with Drogba notably shouting, "It's a fucking disgrace" into a live television camera. Kevin McCarra writing for The Guardian described Øvrebø as "relatively inexperienced" and declared he "did not inspire any confidence whatsoever".
Manchester United won 4–1 on aggregate.
Barcelona 1–1 Chelsea on aggregate. Barcelona won on away goals.