The sides who finished first in each UEFA Cup section were drawn against one of the third-ranked teams from another group while the runners-up in each section were paired with one of the eight clubs joining the competition from the UEFA Champions League group stage. The group winners and runners-up will play their second leg at home, while sides from the same association were kept apart in the draw. The format is two-legged knockout ties with the first legs being played on 18/19 February and the second legs on 26 February. No teams were seeded in the draw for the last 16.

First leg : 18 & 19 February 2009
Second leg : 26 February 2009

Round of 32 draw

Paris Saint-Germain FC (FRA) v VfL Wolfsburg (GER)
FC København (DEN) v Manchester City FC (ENG)
NEC Nijmegen (NED) v Hamburger SV (GER)
UC Sampdoria (ITA) v FC Metalist Kharkiv (UKR)
SC Braga (POR) v R. Standard de Liège (BEL)
Aston Villa FC (ENG) v PFC CSKA Moskva (RUS)
KKS Lech Poznań (POL) v Udinese Calcio (ITA)
Olympiacos CFP (GRE) v AS Saint-Etienne (FRA)
ACF Fiorentina (ITA) v AFC Ajax (NED)
Aalborg BK (DEN) v RC Deportivo La Coruña (ESP)
Werder Bremen (GER) v AC Milan (ITA)
FC Girondins de Bordeaux (FRA) v Galatasaray AŞ (TUR)
FC Dynamo Kyiv (UKR) v Valencia CF (ESP)
FC Zenit St. Petersburg (RUS) v VfB Stuttgart (GER)
Olympique de Marseille (FRA) v FC Twente (NED)
FC Shakhtar Donetsk (UKR) v Tottenham Hotspur FC (ENG)


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