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 shoot-out 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.