Arsenal will face Sporting Lisbon, Azerbaijani side Qarabag and Ukrainian outfit Vorskla Poltava in the Europa League group stage.
They could have to do without playmaker Henrikh Mkhitaryan for the trip to Baku to play Qarabag because of the ongoing conflict between Azerbaijan and Armenia.
The Armenian missed a trip to Azerbaijan to play Gabala in 2015 because of security concerns when he was with Borussia Dortmund.
It will be a first ever meeting against both Qarabag and Vorskla for the Gunners, but they will be hoping history repeats itself when it comes to Sporting.
The last time the Gunners played the Portuguese club was in the November 1969 in the Fairs Cup, a predecessor to the Europa League. They won that match 3-0 and then went on to win the whole tournament.
Sporting saw a mass exodus of players over the summer, with star men such as Rui Patricio and Gelson Martins departing the club, while Qarabag will return to London having faced Tottenham and Chelsea in UEFA competition in recent years.
Elsewhere, Chelsea face long-haul trips after being drawn with Greek side PAOK, Belarusian champions BATE Borisov and Hungarian champions Vidi.
PAOK and BATE were both knocked out of the Champions League at the playoff stage, while Vidi are competing in European competition for the first time since rebranding from Videoton.
Steven Gerrard’s Rangers were dealt a very challenging task after being drawn against Villarreal, Rapid Vienna and Spartak Moscow.
Bundesliga side RB Leipzig and Austrian outfit FC Salzburg, both closely identified with the Red Bull energy drink brand, will meet for the first time in competitive matches after being drawn in the same group.
Leipzig and Salzburg were paired in Group B alongside Scottish champions Celtic and Norwegian side Rosenborg.
UEFA said last year that it was satisfied that Red Bull does not have a controlling influence in both clubs, who wear their corporate colours and are closely identified with the energy drinks manufacturer.
Red Bull bought Austria Salzburg in 2005, renaming it Red Bull Salzburg, and then SSV Markranstaedt in 2009, giving it the name RB Leipzig.
Last year, it successfully argued that, following a restructuring, it no longer has a controlling stake in the Austrian club and merely sponsors it.
Seven-times European champions AC Milan, who won an appeal against a decision to kick them out of the competition for breaking UEFA’s break-even rule, will meet Olympiakos and Real Betis as well as FC Dudelange from Luxembourg.
Group A: Bayer Leverkusen, Ludogorets, Zurich, AEK Larnaca
Group B: FC Salzburg, Celtic, RB Leipzig, Rosenborg
Group C: Zenit, Copenhagen, Bordeaux, Slavia Prague
Group D: Anderlecht, Fenerbache, Dinamo Zagreb, Spartak Tranava
Group E: Arsenal, Sporting Lisbon, Qarabag, Vorskla Poltava
Group F: Olympiakos, AC Milan, Real Betis, F91 Dudelange
Group G: Villarreal, Rapid Vienna, Spartak Moscow, Rangers
Group H: Lazio, Marseille, Eintracht Frankfurt, Apollon Limassol
Group I: Besiktas, Genk, Malmo, Sarpsborg
Group J: Sevilla, Krasnodar, Standard Liege, Akhisarspor
Group K: Dynamo Kiev, Astana, Rennes, Jablonec
Group L: Chelsea, PAOK, BATE Borisov, Vidi
ESPN FC’s Mattias Karen contributed to this report.