Tottenham will face holders Real Madrid in the group stage of the Champions League, while Manchester United will tackle Benfica.
Spurs have been drawn in Group H alongside Spanish side Real, German giants Borussia Dortmund and Apoel Nicosia of Cyprus.
The draw pits Spurs against former stars Gareth Bale and Luka Modric.
Premier League champions Chelsea have been drawn to play Atletico Madrid, Roma and Qarabag in Group C, while Europa League winners United face Benfica, Basle and CSKA Moscow in Group A.
Manchester City are up against Shakhtar Donetsk, Napoli and Feyenoord in Group F, and Liverpool will meet Spartak Moscow, Sevilla and Maribor in Group E.
Scottish champions Celtic face an incredibly tough test in a group with Bayern Munich, Paris St-Germain and Anderlecht.