Manchester United will be reunited with former manager José Mourinho after being drawn to face his Fenerbahce side in the UEFA Europa League.
Mourinho, who won the Europa League while in charge of United in 2017, moved to the Istanbul-based club this summer. United will also face Glasgow Rangers at Old Trafford and a trip to Porto's Estádio do Dragão.
As with the Champions League, UEFA has amended the format by creating an eight-game league phase and expanded the competition to 36 teams.
Unlike in previous years, no teams will drop down from the Champions League after the first round. The dates for the fixtures are set to be announced on Saturday.
Tottenham, meanwhile, will play Daniele De Rossi's Roma at home and also face a trip to Galatasaray.
Rangers were drawn against both United and Tottenham.
With the new format and drawing system, each team was drawn against eight different opponents -- four matches at home, and four away -- two from each of the four seeded pots.
Teams from the same league could not be drawn against each other, and each club can play no more than two teams from one country.
The top eight teams will progress directly to the round of 16. Teams finishing between ninth and 24th place will advance to a knockout playoff stage, while the bottom 12 teams will be eliminated.
In the Conference League, Chelsea were drawn against Gent, Shamrock Rovers, FC Noah, Heidenheim, Astana and Panathinaikos.
Europa League draw:
Manchester United: Rangers (H), Porto (A), PAOK (H) Fenerbache (A), Bodo Glimt (H), Viktoria (A), Twente (H), FCSB (A)
Tottenham Hotspur: Roma (H), Rangers (A), AZ Alkmaar (H), Ferencvaros (A), Qarabag (H), Galatasaray (A), Elfsborg (H), Hoffenheim (A)
Ajax: Lazio (H), Slavia Prague (A), Maccabi Tel-Aviv (A), Real Sociedad (A), Galatasaray (H), Qarabag (A), Besiktas (H), RFS (A)
Roma: Frankfurt (H), Tottenham (A), Braga (H), AZ Alkmaar (A), Dynamo Kiev (H), Union SG (A), Athletic Club (H), Elfsborg (A)
Lazio: Porto (H), Ajax (A), Real Sociedad (H), Braga (A), Ludogorets (H), Kyiv (A), Nice (H), Twente (A)
Rangers: Tottenham (H,) Manchester United (A), Lyon (H), Olympiacos (A), Union SG (H), Malmo (A), FCSB (H), Nice (A)