Real Madrid, AC Milan and Ajax, who have won 20 European Cups between them, will meet in the group stage of the Champions League following Thursday's draw in Monaco.
It is the second consecutive season that nine-time champions Madrid and seven-time winners Milan have been drawn together with Auxerre making up the fourth team in Group G.
Defending champions Inter Milan will play Werder Bremen, Tottenham and FC Twente in Group A, while Barcelona take on Panathinaikos, FC Copenhagen and Rubin Kazan in Group D.
Alex Ferguson, the Manchester United manager, will be reunited with Rangers which he played for in the 1960s. Valencia and Bursaspor of Turkey make up Group C.
Massimiliano Allegri, the AC Milan coach, said: "Facing Real Madrid is very evocative, it's a very stimulating challenge.
"The San Siro and Santiago Bernabeu will be completely full and it's sure to be a show.
"Ajax and Auxerre got through their playoffs brilliantly and are two very worthy opponents.
"We're going to have to maintain our concentration and physical condition for all these games. It's an iron-tough group."
Madrid has not won the competition since 2002 and has not been past the quarter-finals since 2004.
"It is a very difficult group of course, but very attractive for the fans [because] of all the history with these three clubs," Emilio Butragueno, Madrid's director of football, said.
For Jose Mourinho, the draw is an early chance to impress at Madrid after leaving Inter having won the title in May.
"We hope that he is the right man to take the team to the title," Butragueno said.
"Maybe [he wanted] a little easier [group]. But, anyway, we have to face this situation. We are Real Madrid and we will try to do our best."
Ajax, which won the last of its four European Cups in 1995, is back in the Champions League for the first time since 2005 after beating Dynamo Kiev in the playoff round.
"You want to win every match and when you see AC Milan and Real Madrid in the pool, you know it will be tough," Martin Jol, Ajax coach's, said.
It was an intriguing draw for AC Milan midfielder Clarence Seedorf, a two-time winner with the Serie A side who has also won the competition with Madrid and Ajax.
Bayern Munich, last season's losing finalist, are drawn with AS Roma, FC Basel and Cluj in Group E.
Barcelona will be hoping to avoid losing to Russian club Rubin Kazan for a second straight season.
English Premier League champions Chelsea will also be travelling to Russia, to face Spartak Moscow. Marseille and newcomer Zilina are also in Group F.
Arsenal will face former striker Eduardo da Silva when it plays Shakhtar Donetsk, while FC Braga of Portugal and Partizan Belgrade complete Group H.
Lyon, the top-seeded team in Group B, was paired with Benfica, Schalke and Hapoel Tel Aviv.
Matchday one will be played on September 14 to September 15.
Inter Milan, Werder Bremen, Tottenham, FC Twente
Lyon, Benfica, Schalke, Hapoel Tel-Aviv
Manchester United, Valencia, Rangers, Bursaspor
Barcelona, Panathinaikos, FC Copenhagen, Rubin Kazan
Bayern Munich, AS Roma, Basel, CFR Cluj
Chelsea, Marseille, Spartak Moscow, Zilina
AC Milan, Real Madrid, Ajax, Auxerre
Arsenal, Shakhtar Donetsk, Braga, Partizan Belgrade