2008–09 UEFA Cup Round of 16 Round of 16

| Team_1 | Agg_ | 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 St. 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 ) | Aalborg BK | 2–0 | 0–2 ( aet ) |
| Marseille | 4–3 | Ajax | 2–1 | 2–2 ( aet ) |
| Hamburg | 4–3 | Galatasaray | 1–1 | 3–2 |