Tottenham have been drawn against Feyenoord in the last 32 of the Uefa Cup - a repeat of the 1974 final that the Dutch side won 4-2 on aggregate.
Newcastle United have been paired with Belgian side Zulte-Waregem while Blackburn Rovers must play Germany's Bayer Leverkusen.
Rangers will take on Israeli side Hapoel Tel-Aviv.
Holders Seville face a tricky tie against Steaua Bucharest, who finished third in their Champions League group.
The first leg of each tie will take place on 14 or 15 February, with the return on 22 February.
Tottenham manager Martin Jol expects Feyenoord to offer his side a tough test.
Jol told his club's website: "It could have been worse and it could have been better but I am looking forward to going to Rotterdam.
"They are probably not as good as when they played Spurs in the Uefa Cup final in 1974, but it is still a big club.
"It will be difficult going over there because they are strong at home. But we have the advantage of playing the second leg here."
Teams also found out their potential opponents in the last 16.
If they progress, Spurs will face Braga or Parma while Newcastle will play Fenerbahce or AZ Alkmaar.
Blackburn could meet Lens or Panathinaikos while Bordeaux or Osasuna will await Rangers.
Draw for the last 32:
Zulte Waregem v Newcastle
Braga v Parma
Lens v Panathinaikos
Leverkusen v Blackburn
Hapoel Tel Aviv v Rangers
Livorno v Espanyol
Feyenoord v Tottenham
Fenerbahce v AZ Alkmaar
Werder Bremen v Ajax
Spartak Moscow v Celta Vigo
CSKA Moscow v Maccabi Haifa
AEK Athens v PSG
Benfica v Dinamo Bucharest
Steaua Bucharest v Sevilla
Shakhtar v Nancy
Bordeaux v Osasuna
(Ties to be played 14/15 & 22 February)
Draw for the last 16:
Zulte Waregem or Newcastle v Fenerbahce or AZ Alkmaar
CSKA Moscow or Maccabi Haifa v Livorno or Espanyol
Hapoel Tel Aviv or Rangers v Bordeaux or Osasuna
Braga or Parma v Feyenoord or Tottenham
Steaua Bucharest or Sevilla v Shakhtar or Nancy
Lens or Panathinaikos v Leverkusen or Blackburn
AEK Athens or PSG v Benfica or Dinamo Bucharest
Spartak Moscow or Celta Vigo v Werder Bremen or Ajax
(Ties to be played on 8 & 14/15 March)