AC Milan have been drawn against Irish minnows Shamrock Rovers in the Europa League, while Tottenham have been handed a tie against Bulgarian side Lokomotiv Plovdiv.
The second round of qualifying will kick off on September 17, with all fixtures set to be played in a straight knockout format behind closed doors amid the continued threat of coronavirus.
In the tie of the round, Milan will travel to Dublin to take on Republic of Ireland-based Rovers, who set up the glamour encounter by beating Finnish club Ilves on penalties in the previous round.
The Rossoneri were excluded from the competition last term due to Financial Fair Play breaches, but secured sixth place in Serie A to return to the continental stage under Stefano Pioli.
🇮🇪 Shamrock v AC Milan 🇮🇹
— UEFA Europa League (@EuropaLeague) August 31, 2020
🇧🇬 Lokomotiv Plovdiv v Tottenham🏴
🇦🇿 Neftçi v Galatasaray 🇹🇷
Second qualifying round ties: 17 September 👇#UEL
Elsewhere, Spurs will come up against Lokomotiv Plovdiv in Bulgaria, as Jose Mourinho bids to bring to an end to the club's 12-year wait for major silverware.
The Lilywhites missed out on Champions League football for the first time in five years after finishing sixth in the Premier League last term, but will be expected to reach the latter stages of Europe's second-tier competition.
Scottish giants Rangers, currently helmed by Liverpool legend Steven Gerrard, will also be competing in the Europa League in 2020-21, with their first qualifying encounter coming against Lincoln Red Imps in Gibraltar.
Third qualifying round ties: 15/16 September 👇#UCL https://t.co/BafmrIeMev pic.twitter.com/Yz1XWjHjNY
— UEFA Champions League (@ChampionsLeague) August 31, 2020
Rangers' arch-rivals Celtic will join the competition at the next stage, having been knocked out of the Champions League at home by Hungarian outfit Ferencvaros in embarrassing fashion earlier this month.
Two more Scottish clubs are scheduled to join the Gers in the second qualifying round, with Aberdeen set for an away clash against Viking of Norway while Motherwell are due to face Coleraine from Northern Ireland.
The draw for the third round of qualifying for the Champions League also took place on Monday, as Celtic's conquerors Ferencvaros were rewarded with a tie against Dinamo Zagreb.
Benfica will take on PAOK. Jorge Jesus' side will head to Thessaloniki on September 15 or 16 to face the team that knocked out Turkish club Besiktas in the previous round.
Eredivisie side AZ face a visit to Dynamo Kiev, Gent will play Rapid Vienna, Qarabag take on Ole Gunnar Solskjaer's former side Molde, Red Star Belgrade visit Omonia Nicosia and Maccabi Tel-Aviv host Dinamo Brest.
Swiss champions Young Boys head to Denmark to face Midtjylland.
