2008–09 UEFA Cup Round of 32 Round of 32

| Team_1 | Agg_ | Team_2 | _1st_leg | _2nd_leg |
|---|---|---|---|---|
| Paris Saint-Germain | 5–1 | Wolfsburg | 2–0 | 3–1 |
| Copenhagen | 3–4 | Manchester City | 2–2 | 1–2 |
| NEC | 0–4 | Hamburg | 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 |
| Aalborg BK | 6–1 | Deportivo | 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 St. Petersburg | 4–2 | Stuttgart | 2–1 | 2–1 |
| Marseille | 1–1 (7–6 p ) | Twente | 0–1 | 1–0 ( aet ) |
| Shakhtar Donetsk | 3–1 | Tottenham Hotspur | 2–0 | 1–1 |