Villa and Tottenham will both face eastern European opposition, with Aston Villa drawing Russian side CSKA Moscow and Spurs travelling to Ukrainian side Shakhtar Donetsk, who enter the competition having finished third in their Champions League group. Manchester City will play Danish side FC Copenhagen.
Holders FC Zenit St. Petersburg will mark their return to the UEFA Cup with a tough tie against VfB Stuttgart while AC Milan’s quest to win the only major European trophy that has so far eluded them sees them meet Werder Bremen in the Round of 32. Milan have been European champions seven times, and have also won two UEFA Cup Winners’ Cups and five UEFA Super Cups, with the UEFA Cup the only major continental title they have yet to claim.
In other ties, Fiorentina will take on Ajax, Bordeaux meet Galatasaray AŞ and FC Dynamo Kyiv play Valencia CF. The competition’s two surprise packages, FC Metalist Kharkiv and KKS Lech Poznań, both received tough draws against Italian sides. Lech will take on Udinese Calcio, playing the first leg at home, while Metalist visit UC Sampdoria in their first UEFA Cup game of 2009.
The draw for the next round after that was also made and should Villa and Spurs both progress they will meet each other in the last 16.
Last 32 draw (first leg 18-19 Feb/ second leg 26 Feb):
Paris Saint-Germain v Wolfsburg
FC Copenhagen v MANCHESTER CITY
NEC Nijmegen v Hamburg
Sampdoria v Metalist Kharkiv
Braga v Standard Liege
ASTON VILLA v CSKA Moscow
Lech Poznan v Udinese
Olympiakos v Saint-Etienne
Fiorentina v Ajax
Aalborg v Deportivo La Coruna
Werder Bremen v AC Milan
Bordeaux v Galatasaray
Dynamo Kiev v Valencia
Zenit St. Petersburg v Stuttgart
Marseille v FC Twente
Shakhtar Donetsk v TOTTENHAM
Last 16 draw (first leg 12 Mar/ second leg 18-19 Mar):
Werder Bremen or AC Milan v Olympiakos or Saint-Etienne
ASTON VILLA or CSKA Moscow v Shakhtar Donetsk or TOTTENHAM
Lech Poznan or Udinese v Zenit St Petersburg or Stuttgart
Paris Saint-Germain or Wolfsburg v Braga or Standard Liege
Dynamo Kiev or Valencia v Sampdoria or Metalist Kharkiv
Copenhagen or MANCHESTER CITY v Aalborg or Deportivo
Marseille or FC Twente v Fiorentina or Ajax
NEC Nijmegen or Hamburg v Bordeaux or Galatasaray