AC Milan and Fiorentina have been handed tough draws in the UEFA Cup Round of 32 while, Sampdoria and Udinese have been given easier routes to the last 16.
After finishing second behind Wolfsburg in the group stage, Milan face another German opponent in Werder Bremen - who dropped out of the UEFA Champions League. Fiorentina also join the UEFA Cup from the Champions League, but Cesare Prandelli's side have been paired with Dutch giants Ajax.
Sampdoria, who squeezed past Sevilla on Thursday, face Ukrainian outfit Metalist Kharkiv and Udinese play another of the surprise packages, Lech Poznan from Poland.
In other ties, holders Zenit St Petersburg face Stuttgart, Paris Saint-Germain play Wolfsburg, Bordeaux take on Galatasaray, Dynamo Kiev entertain Valencia, Aston Villa meet CSKA Moscow and Marseille host FC Twente.
The Round of 32 matches will be played over two legs on February 18/19 and 26 February for a place in the last 16 - the draw for which was also made in Switzerland today.
UEFA Cup 2008-09
Round of 32 First Leg
Wednesday 18 February 2009
Aalborg v Deportivo La Coruna (2000)
Aston Villa v CSKA Moscow (1900)
Bordeaux v Galatasaray (1945)
Braga v Standard Liege (2045)
Dynamo Kiev v Valencia (1700)
NEC Nijmegen v Hamburg (1945)
Olympiakos v Saint-Etienne (1730)
Paris Saint-Germain v Wolfsburg (1945)
Sampdoria v Metalist Kharkiv (1945)
Werder Bremen v Milan (1935)
Zenit St. Petersburg v Stuttgart (1715)
Thursday 19 February 2009
Copenhagen v Manchester City (1905)
Fiorentina v Ajax (1945)
Lech Poznan v Udinese (1700)
Marseille v Twente (1945)
Shakhtar Donetsk v Tottenham Hotspur (1845)
Round of 32 Second Leg
Thursday 26 February 2009
Ajax v Fiorentina (1945)
CSKA Moscow v Aston Villa (1700)
Deportivo La Coruna v Aalborg (2000)
Galatasaray v Bordeaux (1830)
Hamburg v NEC Nijmegen (1715)
Manchester City v Copenhagen (1945)
Metalist Kharkiv v Sampdoria (1700)
Milan v Werder Bremen (1945)
Saint-Etienne v Olympiakos (1955)
Standard Liege v Braga (1945)
Stuttgart v Zenit St. Petersburg (1945)
Tottenham Hotspur v Shakhtar Donetsk (2000)
Twente v Marseille (1730)
Udinese v Lech Poznan (1945)
Valencia v Dynamo Kiev (2030)
Wolfsburg v Paris Saint-Germain (1800)
UEFA Cup 2008-09
Round of 16 First Leg
Thursday 12 March 2009
Aston Villa/CSKA v Shakhtar/Tottenham
Bremen/Milan v Olympiakos/St-Etienne
Copenhagen/Man City v Aalborg/Deportivo
Dynamo Kiev/Valencia v Sampdoria/Metalist
Lech/Udinese v Zenit/Stuttgart
Marseille/Twente v Fiorentina/Ajax
Nijmegen/Hamburg v Bordeaux/Galatasaray
PSG/Wolfsburg v Braga/Standard
Round of 16 Second Leg
Wednesday 18 & Thursday 19 March 2009
Aalborg/Deportivo v Copenhagen/Man City
Bordeaux/Galatasaray v Nijmegen/Hamburg
Braga/Standard v PSG/Wolfsburg
Fiorentina/Ajax v Marseille/Twente
Olympiakos/St-Etienne v Bremen/Milan
Sampdoria/Metalist v Dynamo Kiev/Valencia
Shakhtar/Tottenham v Aston Villa/CSKA
Zenit/Stuttgart v Lech/Udinese
Source: UEFA
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