2008–09 UEFA Cup knockout stage

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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.

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.

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.^[1]

Group	Winners	Runners-up	Third-placed teams
A	England Manchester City	Netherlands Twente	France Paris Saint-Germain
B	Ukraine Metalist Kharkiv	Turkey Galatasaray	Greece Olympiacos
C	Belgium Standard Liège	Germany VfB Stuttgart	Italy Sampdoria
D	Italy Udinese	England Tottenham Hotspur	Netherlands NEC
E	Germany VfL Wolfsburg	Italy Milan	Portugal Braga
F	Germany Hamburger SV	Netherlands Ajax	England Aston Villa
G	France Saint-Étienne	Spain Valencia	Denmark Copenhagen
H	Russia CSKA Moscow	Spain Deportivo La Coruña	Poland Lech Poznań

Group	Third-placed teams
A	France Bordeaux
B	Germany Werder Bremen
C	Ukraine Shakhtar Donetsk
D	France Marseille
E	Denmark AaB
F	Italy Fiorentina
G	Ukraine Dynamo Kyiv
H	Russia Zenit Saint Petersburg

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.^[2]

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 France	5–1	Germany  VfL Wolfsburg	2–0	3–1
Copenhagen Denmark	3–4	England  Manchester City	2–2	1–2
NEC Netherlands	0–4	Germany  Hamburger SV	0–3	0–1
Sampdoria Italy	0–3	Ukraine  Metalist Kharkiv	0–1	0–2
Braga Portugal	4–1	Belgium  Standard Liège	3–0	1–1
Aston Villa England	1–3	Russia  CSKA Moscow	1–1	0–2
Lech Poznań Poland	3–4	Italy  Udinese	2–2	1–2
Olympiacos Greece	2–5	France  Saint-Étienne	1–3	1–2
Fiorentina Italy	1–2	Netherlands  Ajax	0–1	1–1
AaB Denmark	6–1	Spain  Deportivo La Coruña	3–0	3–1
Werder Bremen Germany	3–3 (a)	Italy  Milan	1–1	2–2
Bordeaux France	3–4	Turkey  Galatasaray	0–0	3–4
Dynamo Kyiv Ukraine	3–3 (a)	Spain  Valencia	1–1	2–2
Zenit Saint Petersburg Russia	4–2	Germany  VfB Stuttgart	2–1	2–1
Marseille France	1–1 (7–6 p)	Netherlands  Twente	0–1	1–0 (a.e.t.)
Shakhtar Donetsk Ukraine	3–1	England  Tottenham Hotspur	2–0	1–1

3–3 on aggregate; Dynamo Kyiv won on away goals.

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Zenit Saint Petersburg won 4–2 on aggregate.

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Saint-Étienne won 5–2 on aggregate.

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CSKA Moscow won 3–1 on aggregate.

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3–3 on aggregate; Werder Bremen won on away goals.

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Metalist Kharkiv won 3–0 on aggregate.

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Hamburger SV won 4–0 on aggregate.

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Paris Saint-Germain won 5–1 on aggregate.

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Galatasaray won 4–3 on aggregate.

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AaB won 6–1 on aggregate.

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Braga won 4–1 on aggregate.

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Udinese won 4–3 on aggregate.

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Shakhtar Donetsk won 3–1 on aggregate.

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Manchester City won 4–3 on aggregate.

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1–1 on aggregate; Marseille won 7–6 on penalties.

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Ajax won 2–1 on aggregate.

The draw for the round of 16 took place on 19 December 2008, immediately after the draw for the round of 32.^[2]

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 Germany	3–2	France  Saint-Étienne	1–0	2–2
CSKA Moscow Russia	1–2	Ukraine  Shakhtar Donetsk	1–0	0–2
Udinese Italy	2–1	Russia  Zenit Saint Petersburg	2–0	0–1
Paris Saint-Germain France	1–0	Portugal  Braga	0–0	1–0
Dynamo Kyiv Ukraine	3–3 (a)	Ukraine  Metalist Kharkiv	1–0	2–3
Manchester City England	2–2 (4–3 p)	Denmark  AaB	2–0	0–2 (a.e.t.)
Marseille France	4–3	Netherlands  Ajax	2–1	2–2 (a.e.t.)
Hamburger SV Germany	4–3	Turkey  Galatasaray	1–1	3–2

3–3 on aggregate; Dynamo Kyiv won on away goals.

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Shakhtar Donetsk won 2–1 on aggregate.

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Hamburger SV won 4–3 on aggregate.

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Paris Saint-Germain won 1–0 on aggregate.

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Werder Bremen won 3–2 on aggregate.

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Marseille won 4–3 on aggregate.

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2–2 on aggregate; Manchester City won 4–3 on penalties.

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Udinese won 2–1 on aggregate.

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

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 Germany	4–3	England  Manchester City	3–1	1–2
Paris Saint-Germain France	0–3	Ukraine  Dynamo Kyiv	0–0	0–3
Shakhtar Donetsk Ukraine	4–1	France  Marseille	2–0	2–1
Werder Bremen Germany	6–4	Italy  Udinese	3–1	3–3

Shakhtar Donetsk won 4–1 on aggregate.

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Hamburger SV won 4–3 on aggregate.

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Dynamo Kyiv won 3–0 on aggregate.

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Werder Bremen won 6–4 on aggregate.

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

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 Germany	3–3 (a)	Germany  Hamburger SV	0–1	3–2
Dynamo Kyiv Ukraine	2–3	Ukraine  Shakhtar Donetsk	1–1	1–2

Shakhtar Donetsk won 3–2 on aggregate.

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3–3 on aggregate; Werder Bremen won on away goals.

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

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