Manchester United's stern test in the group stage of the Champions League has been compounded by a fixture list which sees them play two massive Premier League clashes immediately after long trips to Turkey and Russia.
United were drawn in Group B with Turkish side Besiktas, CSKA Moscow and German champions Wolfsburg. Sir Alex Ferguson now faces a major headache with United at home to Manchester City after travelling to Istanbul and away at Liverpool four days after their Moscow journey.
"These are difficult ties, especially the trips to Russia and Turkey," said Ferguson. "CSKA have developed strongly in the last few years and games in Turkey are always difficult."
He added: "We also know the quality that we're up against with Wolfsburg, with what they achieved in the Bundesliga last season."
The British clubs all avoided the European heavyweights of Barcelona, Real Madrid and the Milan sides.
Chelsea are in Group D with Porto, Atletico Madrid and Apoel Nicosia, Liverpool face Lyon, Fiorentina and Debreceni in Group E, while Arsenal have perhaps the easiest task with AZ Alkmaar, Olympiacos and Standard Liege in Group H.
Rangers were drawn against Sevilla, Stuttgart and Romanian champions Unirea Urziceni - coached by Dan Petrescu - in Group G.
Liverpool manager Rafael Benitez said: "The important thing as always is that the travelling isn't too bad, we don't have too far to go for any of the games.
"Lyon might not have won the league last season but before that they won it many years in a row, so we know they have lots of good players who can play good football," he told the club's official website.
"Fiorentina are an historic club and if Debreceni have won their league then we know it means it's because they're a good side."