*AaB Aalborg 6-1 Deportivo La Coruña
| 26.02.2009 | Deportivo La Coruña | 1-3 | AaB Aalborg | |
| 18.02.2009 | AaB Aalborg | 3-0 | Deportivo La Coruña | |
*Werder Bremen 3-3 AC Milan
| 26.02.2009 | AC Milan | 2-2 | Werder Bremen | |
| 18.02.2009 | Werder Bremen | 1-1 | AC Milan | |
Aston Villa 1-3 CSKA Moscow *
| 26.02.2009 | CSKA Moscow | 2-0 | Aston Villa | |
| 18.02.2009 | Aston Villa | 1-1 | CSKA Moscow | |
*Dynamo Kyiv 3-3 Valencia CF
| 26.02.2009 | Valencia CF | 2-2 | Dynamo Kyiv | |
| 18.02.2009 | Dynamo Kyiv | 1-1 | Valencia CF | |
FC København 3-4 Manchester City *
| 26.02.2009 | Manchester City | 2-1 | FC København | |
| 19.02.2009 | FC København | 2-2 | Manchester City | |
Fiorentina 1-2 AFC Ajax *
| 26.02.2009 | AFC Ajax | 1-1 | Fiorentina | |
| 19.02.2009 | Fiorentina | 0-1 | AFC Ajax | |
Girondins Bordeaux 3-4 Galatasaray SK *
| 26.02.2009 | Galatasaray SK | 4-3 | Girondins Bordeaux | |
| 18.02.2009 | Girondins Bordeaux | 0-0 | Galatasaray SK | |
NEC Nijmegen 0-4 Hamburger SV *
| 26.02.2009 | Hamburger SV | 1-0 | NEC Nijmegen | |
| 18.02.2009 | NEC Nijmegen | 0-3 | Hamburger SV | |
Olympiakos Pireus 2-5 AS Saint-Étienne *
| 26.02.2009 | AS Saint-Étienne | 2-1 | Olympiakos Pireus | |
| 18.02.2009 | Olympiakos Pireus | 1-3 | AS Saint-Étienne | |
*Olympique Marseille 1-1 FC Twente
| 26.02.2009 | FC Twente | 0-1/p.6-7 | Olympique Marseille | |
| 19.02.2009 | Olympique Marseille | 0-1 | FC Twente | |
*Paris St. Germain 5-1 VfL Wolfsburg
| 26.02.2009 | VfL Wolfsburg | 1-3 | Paris St. Germain | |
| 18.02.2009 | Paris St. Germain | 2-0 | VfL Wolfsburg | |
Sampdoria 0-3 Metalist Kharkiv *
| 26.02.2009 | Metalist Kharkiv | 2-0 | Sampdoria | |
| 18.02.2009 | Sampdoria | 0-1 | Metalist Kharkiv | |
*Shakhtar Donetsk 3-1 Tottenham
| 26.02.2009 | Tottenham | 1-1 | Shakhtar Donetsk | |
| 19.02.2009 | Shakhtar Donetsk | 2-0 | Tottenham | |
*SC Braga 4-1 Standard Liège
| 26.02.2009 | Standard Liège | 1-1 | SC Braga | |
| 18.02.2009 | SC Braga | 3-0 | Standard Liège | |
Lech Poznan 3-4 Udinese Calcio *
| 26.02.2009 | Udinese Calcio | 2-1 | Lech Poznan | |
| 19.02.2009 | Lech Poznan | 2-2 | Udinese Calcio | |
*Zenit 4-2 VfB Stuttgart
| 26.02.2009 | VfB Stuttgart | 1-2 | Zenit | |
| 18.02.2009 | Zenit | 2-1 | VfB Stuttgart | |