Leeds United will face Roma, third in Italy's Serie A, and Arsenal have been handed a tie against Deportivo La Coruna, the leaders of the Spanish Primera Division.
For Leeds the tie is a repeat of last season's second round when they lost 1-0 on aggregate, with Marco Delvecchio's 17th-minute strike in the first leg at the Olympic Stadium the dividing factor.
Peter Ridsdale, the Leeds chairman, predicted revenge for his club over the two legs, the first of which will be played in the Italian capital on 2 March. "At least this time it's a team we do know, particularly as they also played Newcastle in the last round [again winning 1-0 on aggregate], but I think we can beat them this time.
"We are a lot more experienced than a year ago. We're playing well and we are top of the Premiership, so we have to feel confident." Should Leeds win they will face Udinese or Slavia Prague in the quarter-finals.
Roma - under Fabio Capello this season - have been impressive this season and are only behind Lazio and Juventus in Serie A. But Capello fears United and said: "There were two teams I wanted to avoid in the draw - Celta Vigo and Leeds. I'm not saying that we embark upon this venture defeated, but it will be a very hard game."
The Leeds manager, David O'Leary, meanwhile, is unhappy with Uefa because he believes the draw was weighted in favour of "the big boys". The seeding process left Leeds facing a tie against Roma, Juventus, Parma, or the French League leaders Monaco.
"All along the Uefa Cup has been set up for one of the big boys to win it, and here is further evidence of that," said O'Leary. "They were all cosseted together and kept apart from each other to be unleashed on the little fellows. It's a joke."
Arsenal face Deportivo at home first with the second leg a week later in Spain, and should they progress they will meet Parma, the team Arsenal beat to win the Cup-winners' Cup in 1994, in the quarter-finals provided the Italian side have disposed of Germany's Werder Bremen.
"It is one of the toughest draws we could have - and I am only talking about Deportivo at this stage," Arsene Wenger, the Arsenal manager, said. "They are 10 points clear of Barcelona in Spain and have some excellent players, but it is a challenge that we don't mind. You have to play the strongest sides sooner or later if you want to win the Cup and after missing out again in the Champions' League we have real ambition in this competition."
Wenger, though, is doubtful that his Dutch striker Dennis Bergkamp will be able to make the second-leg on Spain's north-east coast because of his fear of flying. Patrick Vieira, the French midfielder, will miss the home leg through suspension.
Javier Irureta, Deportivo's coach, predicted the game will be "the tie of the round". He added: "They were the toughest side we could have got but I'm not unhappy with the draw because English football is very open and competitive."
UEFA CUP DRAW
Parma (It) v Werder Bremen (Ger); Juventus (It) v Celta Vigo (Sp); Roma (It) v Leeds Utd; Real Mallorca (Sp) v Monaco (Fr); Slavia Prague (Cz Rep) v Udinese (It); Borussia Dortmund (Ger) v Galatasaray (Turk); Atletico Madrid (Sp) v Lens (Fr); Arsenal v Deportivo La Coruna (Sp). (To be played 2 and 9 March).
Real Mallorca or Monaco v Borussia Dortmund or Galatasaray; Arsenal or Deportivo La Coruna v Parma or Werder Bremen; Juventus or Celta Vigo v Atletico Madrid or Lens; Roma or Leeds Utd v Slavia Prague or Udinese. (To be played 16 and 23 March).Reuse content