Bolton and Aberdeen must prepare for two of the toughest assignments in the last 32 of the Uefa Cup after being paired with Atletico Madrid and Bayern Munich respectively.
But the news was better for Bolton's fellow Premier League sides Everton and Tottenham.
The Toffees will meet Brann Bergen of Norway and Spurs will play Czech side Slavia Prague.
Rangers, who drop down into the competition after finishing third in their Champions League group, have been paired with Greek outfit Panathinaikos.
Last 32
Aberdeenv Bayern Munich
AEK Athens v Getafe
Boltonv Athletico Madrid
Zenit St Petersberg v Villarreal
Galatasaray v Bayer Leverkusen
Anderlecht v Bordeaux
SK Brann v
Everton
FC Zurich v Hamburg
Rangersv Panathinaikos
PSV Eindhoven v Helsingborgs
Slavia Prague v
Tottenham
Rosenborg v Fiorentina
Sporting v Basle
Werder Bremen v Braga
Benfica v Nurnberg
Marseille v Spartak Moscow
Games to be played: 13, 14 and 20 Feb
Round of 16
Anderlecht/Bordeaux v Aberdeen/Bayern Munich
Rangers/Panathinaikos v Werder Bremen/Braga
Bolton/Athletico Madrid v Sporting/Basle
Galatasaray/Bayer Leverkusen v FC Zurich/Hamburg
AEK Athens/Getafe v Benfica/Nurnberg
Rosenborg/Fiorentina v SK Brann/Everton
Slavia Prague/Tottenham v PSV Eindhoven/Helsingborgs
Marseille/Spartak Moscow v Zenit St Petersberg/Villarreal
Games to be played: Games to be played: 6, 12 and 13 of March