Tottenham will play Ludogorets, LASK and Royal Antwerp in the Europa League group stage.
Spurs were in pot 1 for the draw, held in Switzerland on Friday afternoon, and were drawn in Group J.
Bulgarian club Ludogorets have history against English opposition in Europe, having shared a group with Liverpool in the 2014/15 Champions League and Arsenal in the 2016/17 edition of the competition.
Austria’s LASK, meanwhile, were comfortably beaten by Manchester United in the Europa League round of 16 last season – 7-1 losers on aggregate.
Royal Antwerp are making their debut in the group stage of the competition, having won the Belgian Cup last term.
Jose Mourinho’s Spurs were well beaten 4-0 over two legs by RB Leizpig in the Champions League knockout stages last season, but managed to finish sixth in the Premier League to qualify for Europe.
They will be a force to be reckoned with after adding Gareth Bale to their ranks among other reinforcements this summer.
Here is the Europa League group-stage draw in full:
Group A: AS Roma, Young Boys, CFR Cluj, CSKA Sofia.
Group B: Arsenal, Rapid Wien, Molde, Dundalk.
Group C: Bayer Leverkusen, Slavia Prague, Hapoel Be’er Sheva, Nice.
Group D: Benfica, Standard Liege, Rangers, Lech.
Group E: PSV Eindhoven, PAOK, Granada, Omonoia.
Group F: Napoli, Real Sociedad, AZ Alkmaar, Rijeka.
Group G: Braga, Leicester City, AEK Athens, Zorya Luhansk.
Group H: Celtic, Sparta Prague, AC Milan, Lille.
Group I: Villarreal, Qarabag, Maccabi Tel-Aviv, Sivasspor.
Group J: Tottenham Hotspur, Ludogorets, LASK, Antwerp.
Group K: CSKA Moscow, Dinamo Zagreb, Feyenoord, Wolsberg.
Group L: Gent, Crvena Zvezda, Hoffenheim, Liberec.
Group stage dates
22 October: Group stage, Matchday 1
29 October: Group stage, Matchday 2
5 November: Group stage, Matchday 3
26 November: Group stage, Matchday
3 December: Group stage, Matchday 5
10 December: Group stage, Matchday 6