Competition favourites AC Milan will face Werder Bremen, one of the Champions League dropouts, in the last 32 of the UEFA Cup following Friday's draw in Nyon, Switzerland.
The Italians, seven times European champions but who have never won the UEFA Cup, were sure to meet one of the Champions League third-place finishers after their 2-2 home draw with VfL Wolfsburg on Wednesday allowed the German side to top their qualifying group.
Bremen finished behind Panathinaikos and Inter Milan in their Champions League group.
Wolfsburg's reward is a game against Paris St Germain, who sneaked through on goal difference thanks to their 4-0 win over Twente Enschede in their final group game this week.
If Milan progress they will meet either Olympiakos Piraeus or St Etienne in the last 16 after the draw for that round was also carried out at UEFA headquarters.
Holders Zenit St Petersburg, back in the competition after finishing third behind Real Madrid and Juventus in their Champions League group, were drawn against VfB Stuttgart in the first knockout round.
If Zenit win they will play either Udinese or Polish outsiders Lech Poznan.
Four-times European champions Ajax Amsterdam will play Fiorentina, semi-finalists last season who currently going well in fifth place in Serie A.
The last-32 ties will be played over two legs on Feb 18/19 and Feb. 26. The final is in Istanbul on May 20.