# 2008–09 UEFA Cup knockout stage

The knockout stage of the 2008–09 UEFA Cup began on 18 February 2009, and concluded with the final at the Şükrü Saracoğlu Stadium in Istanbul on 20 May 2009. The final phase involved the 24 teams that finished in the top three in each group in the group stage and the eight teams that finished in third place in the UEFA Champions League group stage.

## Format

Each tie in the final phase, apart from the final, was played over two legs, with each team playing one leg at home. The team that had the higher aggregate score over the two legs progressed to the next round. In the event that aggregate scores finished level, the team that scored more goals away from home over the two legs progressed. If away goals are also equal, 30 minutes of extra time were played. If goals were scored during extra time and the aggregate score was still level, the visiting team qualified by virtue of more away goals scored. If no goals were scored during extra time, there would be a penalty shootout after extra time.
The draw mechanism for each round is as follows:
* In the draw for the round of 32, matches were played between the winner of one group and the third-placed team of a different group, and between the runners-up of one group and the third-placed team from a Champions League group, with the group winner and runner-up host the second leg. Teams from the same national association or have played in the same group in the group stages cannot be drawn together.
* From the round of 16 onwards, these restrictions did not apply, and teams from same group or same association could be drawn together.
In the final, the tie was played over just one leg at a neutral venue. If scores were level at the end of normal time in the final, extra time was played, followed by penalties if scores had remained tied.

## Qualified teams

The knockout stage involved 32 teams: the 24 teams which qualified as the winners, runners-up and third-placed teams of each of the eight groups in the group stage, and the eight third-placed teams from the Champions League group stage.

### UEFA Cup group stage top-three teams

| Group | Winners | Runners-up | Third-placed teams |
| A | Manchester City | Twente | Paris Saint-Germain |
| B | Metalist Kharkiv | Galatasaray | Olympiacos |
| C | Standard Liège | VfB Stuttgart | Sampdoria |
| D | Udinese | Tottenham Hotspur | NEC |
| E | VfL Wolfsburg | Milan | Braga |
| F | Hamburger SV | Ajax | Aston Villa |
| G | Saint-Étienne | Valencia | Copenhagen |
| H | CSKA Moscow | Deportivo La Coruña | Lech Poznań |

### Champions League group stage third-placed teams

| Group | Third-placed teams |
| A | Bordeaux |
| B | Werder Bremen |
| C | Shakhtar Donetsk |
| D | Marseille |
| E | AaB |
| F | Fiorentina |
| G | Dynamo Kyiv |
| H | Zenit Saint Petersburg |

## Bracket

| Round of 32 | Round of 32 | Round of 32 | Round of 32 | Round of 32 | Round of 16 | Round of 16 | Round of 16 | Round of 16 | Round of 16 | Quarter-finals | Quarter-finals | Quarter-finals | Quarter-finals | Quarter-finals | Semi-finals | Semi-finals | Semi-finals | Semi-finals | Semi-finals | Final | Final | Final |
| Paris Saint-Germain | Paris Saint-Germain | 2 | 3 | 5 | | | | | | | | | | | | | | | | | | |
| VfL Wolfsburg | VfL Wolfsburg | 0 | 1 | 1 | Paris Saint-Germain | Paris Saint-Germain | 0 | 1 | 1 | | | | | | | | | | | |
| Braga | Braga | 3 | 1 | 4 | Braga | Braga | 0 | 0 | 0 | | | | | | | | | | | | | |
| Standard Liège | Standard Liège | 0 | 1 | 1 | | | | | | Paris Saint-Germain | Paris Saint-Germain | 0 | 0 | 0 | | | | | | |
| Dynamo Kyiv (a) | Dynamo Kyiv (a) | 1 | 2 | 3 | | | | | | Dynamo Kyiv | Dynamo Kyiv | 0 | 3 | 3 | | | | | | |
| Valencia | Valencia | 1 | 2 | 3 | Dynamo Kyiv (a) | Dynamo Kyiv (a) | 1 | 2 | 3 | | | | | | | | | | | | | |
| Sampdoria | Sampdoria | 0 | 0 | 0 | Metalist Kharkiv | Metalist Kharkiv | 0 | 3 | 3 | | | | | | | | | | | | | |
| Metalist Kharkiv | Metalist Kharkiv | 1 | 2 | 3 | | | | | | | | | | | Dynamo Kyiv | Dynamo Kyiv | 1 | 1 | 2 | |
| Aston Villa | Aston Villa | 1 | 0 | 1 | | | | | | | | | | | Shakhtar Donetsk | Shakhtar Donetsk | 1 | 2 | 3 | |
| CSKA Moscow | CSKA Moscow | 1 | 2 | 3 | CSKA Moscow | CSKA Moscow | 1 | 0 | 1 | | | | | | | | | | | | | |
| Shakhtar Donetsk | Shakhtar Donetsk | 2 | 1 | 3 | Shakhtar Donetsk | Shakhtar Donetsk | 0 | 2 | 2 | | | | | | | | | | | | | |
| Tottenham Hotspur | Tottenham Hotspur | 0 | 1 | 1 | | | | | | Shakhtar Donetsk | Shakhtar Donetsk | 2 | 2 | 4 | | | | | | |
| Marseille (p) | Marseille (p) | 0 | 1 | 1 (7) | | | | | | Marseille | Marseille | 0 | 1 | 1 | | | | | | |
| Twente | Twente | 1 | 0 | 1 (6) | Marseille (a.e.t.) | Marseille (a.e.t.) | 2 | 2 | 4 | | | | | | | | | | | | | |
| Fiorentina | Fiorentina | 0 | 1 | 1 | Ajax | Ajax | 2 | 1 | 3 | | | | | | | | | | | 20 May – Istanbul | 20 May – Istanbul | 20 May – Istanbul |
| Ajax | Ajax | 1 | 1 | 2 | | | | | | | | | | | | | | | | Shakhtar Donetsk (a.e.t.) | Shakhtar Donetsk (a.e.t.) | 2 |
| Werder Bremen (a) | Werder Bremen (a) | 1 | 2 | 3 | | | | | | | | | | | | | | | | Werder Bremen | Werder Bremen | 1 |
| Milan | Milan | 1 | 2 | 3 | Werder Bremen | Werder Bremen | 1 | 2 | 3 | | | | | | | | | | | | | |
| Olympiacos | Olympiacos | 1 | 1 | 2 | Saint-Étienne | Saint-Étienne | 0 | 2 | 2 | | | | | | | | | | | | | |
| Saint-Étienne | Saint-Étienne | 2 | 3 | 5 | | | | | | Werder Bremen | Werder Bremen | 3 | 3 | 6 | | | | | | | | |
| Lech Poznań | Lech Poznań | 2 | 1 | 3 | | | | | | Udinese | Udinese | 1 | 3 | 4 | | | | | | | | |
| Udinese | Udinese | 2 | 2 | 4 | Udinese | Udinese | 2 | 0 | 2 | | | | | | | | | | | | | |
| Zenit Saint Petersburg | Zenit Saint Petersburg | 2 | 2 | 4 | Zenit Saint Petersburg | Zenit Saint Petersburg | 0 | 1 | 1 | | | | | | | | | | | | | |
| VfB Stuttgart | VfB Stuttgart | 1 | 1 | 2 | | | | | | | | | | | Werder Bremen (a) | Werder Bremen (a) | 0 | 3 | 3 | | | |
| NEC | NEC | 0 | 0 | 0 | | | | | | | | | | | Hamburger SV | Hamburger SV | 1 | 2 | 3 | | | |
| Hamburger SV | Hamburger SV | 3 | 1 | 4 | Hamburger SV | Hamburger SV | 1 | 3 | 4 | | | | | | | | | | | | | |
| Bordeaux | Bordeaux | 0 | 3 | 3 | Galatasaray | Galatasaray | 1 | 2 | 3 | | | | | | | | | | | | | |
| Galatasaray | Galatasaray | 0 | 4 | 4 | | | | | | Hamburger SV | Hamburger SV | 3 | 1 | 4 | | | | | | | | |
| Copenhagen | Copenhagen | 2 | 1 | 3 | | | | | | Manchester City | Manchester City | 1 | 2 | 3 | | | | | | | | |
| Manchester City | Manchester City | 2 | 2 | 4 | Manchester City (p) | Manchester City (p) | 2 | 0 | 2 (4) | | | | | | | | | | | | | |
| AaB | AaB | 3 | 3 | 6 | AaB | AaB | 0 | 2 | 2 (3) | | | | | | | | | | | | | |
| Deportivo La Coruña | Deportivo La Coruña | 0 | 1 | 1 | | | | | | | | | | | | | | | | | | |

## Round of 32

The draw for the round of 32 took place on 19 December 2008, the day after the final round of UEFA Cup group stage matches.

### Summary

The first legs were played on 18 February and 19 February, and the second leg matches were played on 26 February 2009.
Manchester City were the only team from the first qualifying round to reach the round of 16. Braga were the only team from the Intertoto Cup to reach the round of 16 and were therefore awarded the title of Intertoto Cup winners. Of the eight teams who had been placed in Pot 5 of the group stage draw, only Metalist Kharkiv and Saint-Étienne reached the round of 16. Of the eight teams that entered the Round of the 32 from the UEFA Champions League group stage, two lost: Fiorentina and Bordeaux. Of the eight ties between a third-placed team and a first-placed team from the UEFA Cup group stage, two were won by the third-placed team; the winners were Braga and Paris Saint-Germain.
| Team 1 | Agg. Tooltip Aggregate score | Team 2 | 1st leg | 2nd leg |
| Paris Saint-Germain | 5–1 | VfL Wolfsburg | 2–0 | 3–1 |
| Copenhagen | 3–4 | Manchester City | 2–2 | 1–2 |
| NEC | 0–4 | Hamburger SV | 0–3 | 0–1 |
| Sampdoria | 0–3 | Metalist Kharkiv | 0–1 | 0–2 |
| Braga | 4–1 | Standard Liège | 3–0 | 1–1 |
| Aston Villa | 1–3 | CSKA Moscow | 1–1 | 0–2 |
| Lech Poznań | 3–4 | Udinese | 2–2 | 1–2 |
| Olympiacos | 2–5 | Saint-Étienne | 1–3 | 1–2 |
| Fiorentina | 1–2 | Ajax | 0–1 | 1–1 |
| AaB | 6–1 | Deportivo La Coruña | 3–0 | 3–1 |
| Werder Bremen | 3–3 (a) | Milan | 1–1 | 2–2 |
| Bordeaux | 3–4 | Galatasaray | 0–0 | 3–4 |
| Dynamo Kyiv | 3–3 (a) | Valencia | 1–1 | 2–2 |
| Zenit Saint Petersburg | 4–2 | VfB Stuttgart | 2–1 | 2–1 |
| Marseille | 1–1 (7–6 p) | Twente | 0–1 | 1–0 (a.e.t.) |
| Shakhtar Donetsk | 3–1 | Tottenham Hotspur | 2–0 | 1–1 |

### Matches

3–3 on aggregate; Dynamo Kyiv won on away goals.
Zenit Saint Petersburg won 4–2 on aggregate.
Saint-Étienne won 5–2 on aggregate.
CSKA Moscow won 3–1 on aggregate.
3–3 on aggregate; Werder Bremen won on away goals.
Metalist Kharkiv won 3–0 on aggregate.
Hamburger SV won 4–0 on aggregate.
Paris Saint-Germain won 5–1 on aggregate.
Galatasaray won 4–3 on aggregate.
AaB won 6–1 on aggregate.
Braga won 4–1 on aggregate.
Udinese won 4–3 on aggregate.
Shakhtar Donetsk won 3–1 on aggregate.
Manchester City won 4–3 on aggregate.
1–1 on aggregate; Marseille won 7–6 on penalties.
Ajax won 2–1 on aggregate.

## Round of 16

The draw for the round of 16 took place on 19 December 2008, immediately after the draw for the round of 32.

### Summary

The first leg matches were played on 12 March, and the second leg matches were played on 18 March and 19 March 2009.
| Team 1 | Agg. Tooltip Aggregate score | Team 2 | 1st leg | 2nd leg |
| Werder Bremen | 3–2 | Saint-Étienne | 1–0 | 2–2 |
| CSKA Moscow | 1–2 | Shakhtar Donetsk | 1–0 | 0–2 |
| Udinese | 2–1 | Zenit Saint Petersburg | 2–0 | 0–1 |
| Paris Saint-Germain | 1–0 | Braga | 0–0 | 1–0 |
| Dynamo Kyiv | 3–3 (a) | Metalist Kharkiv | 1–0 | 2–3 |
| Manchester City | 2–2 (4–3 p) | AaB | 2–0 | 0–2 (a.e.t.) |
| Marseille | 4–3 | Ajax | 2–1 | 2–2 (a.e.t.) |
| Hamburger SV | 4–3 | Galatasaray | 1–1 | 3–2 |

### Matches

3–3 on aggregate; Dynamo Kyiv won on away goals.
Shakhtar Donetsk won 2–1 on aggregate.
Hamburger SV won 4–3 on aggregate.
Paris Saint-Germain won 1–0 on aggregate.
Werder Bremen won 3–2 on aggregate.
Marseille won 4–3 on aggregate.
2–2 on aggregate; Manchester City won 4–3 on penalties.
Udinese won 2–1 on aggregate.

## Quarter-finals

The draw for the quarter-finals took place on 20 March 2009.

### Summary

The first legs were played on 9 April and the second legs were played on 16 April.
| Team 1 | Agg. Tooltip Aggregate score | Team 2 | 1st leg | 2nd leg |
| Hamburger SV | 4–3 | Manchester City | 3–1 | 1–2 |
| Paris Saint-Germain | 0–3 | Dynamo Kyiv | 0–0 | 0–3 |
| Shakhtar Donetsk | 4–1 | Marseille | 2–0 | 2–1 |
| Werder Bremen | 6–4 | Udinese | 3–1 | 3–3 |

### Matches

Shakhtar Donetsk won 4–1 on aggregate.
Hamburger SV won 4–3 on aggregate.
Dynamo Kyiv won 3–0 on aggregate.
Werder Bremen won 6–4 on aggregate.

## Semi-finals

The draw for the semi-finals took place on 20 March 2009, immediately after the draw for the quarter-finals.

### Summary

The first legs were played on 30 April and the second legs on 7 May.
| Team 1 | Agg. Tooltip Aggregate score | Team 2 | 1st leg | 2nd leg |
| Werder Bremen | 3–3 (a) | Hamburger SV | 0–1 | 3–2 |
| Dynamo Kyiv | 2–3 | Shakhtar Donetsk | 1–1 | 1–2 |

### Matches

Shakhtar Donetsk won 3–2 on aggregate.
3–3 on aggregate; Werder Bremen won on away goals.

## Final

The final was played on 20 May 2009 at the Şükrü Saracoğlu Stadium in Istanbul, Turkey.