Tottenham will face holders Real Madrid in the Champions League group stages.
Spurs were drawn in Group H alongside the Spanish giants, German side Borussia Dortmund and Apoel of Cyprus.
The draw pits the Premier League runners-up against Wales winger Gareth Bale, who left Spurs for Real in 2013.
Spurs start at Wembley against Dortmund, before travelling to Cyprus and Spain. They then host Real and visit Germany before ending the group stage of the competition against Apoel.
Scottish champions Celtic face a tough test in a group with Bayern Munich, Paris St-Germain and Anderlecht.
Brendan Rodgers’ side host PSG, then travel to Belgium, before a double header with Bayern. They then go to Paris before hosting Anderlecht in Group B.
Premier League champions Chelsea have been drawn to play Atletico Madrid, Roma and Qarabag in Group C – starting their campaign at home against the Azerbaijan champions.
And Europa League winners Manchester United face Benfica, Basel and CSKA Moscow in Group A, with their first match at home against the Swiss.
Manchester City, who finished third in the Premier League last season, are up against Shakhtar Donetsk, Napoli and Feyenoord in Group F – starting against the Dutch champions.
While Liverpool, who beat Hoffenheim in a play-off to secure their place in the draw in Monaco, will meet Spartak Moscow, Sevilla and Maribor in Group E, with the Spanish side visiting Anfield first.
The group stages begin on 12-13 September.