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.
The draw in Nyon also set up potential last-16 clashes - and this time there were enticing possible fixtures for Everton and Tottenham.
If the Toffees progress to the next stage they could play Italians Fiorentina, who must first beat Rosenborg.
Juande Ramos, twice a winner of this competition with Sevilla, faces the tough prospect of being paired with Dutch side PSV Eindhoven if his Spurs side overcome Slavia.
Should Bolton upset the odds by defeating a talented Atletico side they face a meeting with Sporting Lisbon or FC Basle.
Aberdeen, meanwhile, can look forward to another testing encounter - against one of Anderlecht or Bordeaux - should they oust Bayern and Rangers will be looking forward to a match against one of Bundesliga side Werder Bremen or Braga of Portugal.
Bolton chief executive Allan Duckworth told Sky Sports News: "It's a big one but they all are at this stage so we are pleased to be going to Spain.
"It's a formidable challenge but one that Gary Megson will relish so we are looking forward to that."
Tottenham sporting director Damien Comolli insists they won't underestimate Slavia Prague.
Slavia dropped into the UEFA Cup after finishing third in their Champions League group behind Sevilla and Arsenal.
Comolli said: "We played them last year and know how difficult it was, we won there and at home but it was a tough game especially over there.
"So we know it's difficult, they've had some good results in the Champions League. It is going to be difficult but we knew that before."
Everton manager David Moyes admits he is in the dark about Brann.
He said: "It is hard to tell whether it is a good or a bad draw. I don't know a lot about them.
"Perhaps it could have been a lot worse. But they are the Norwegian champions, so if you look at it from that angle it is a difficult game.
"We will treat them with respect and look forward to the match."
Rangers manager Walter Smith, meanwhile, believes his side's tie against Panathinaikos will be a tricky hurdle to overcome.
He said: "It's a difficult one in the sense that going away to any of the Greek teams is always going to be difficult.
"There's always a very hostile atmosphere in the matches.
"They are always a good standard of team. We've already seen that when they came to Aberdeen to play. So it'll be a tough enough draw."
Aberdeen boss Jimmy Calderwood revealed his players jumped for joy when they were paired against Bayern Munich.
He said: "It's not a fear thing, you have got to respect them, they are a massive name in European football.
"It's a wonderful challenge for the lads. When the draw was made, the lads were jumping up and down so they were well pleased."
Bayern midfielder Mark van Bommel said: "Aberdeen is an attractive opponent and there will certainly be a great atmosphere at both games and I am looking forward to it."