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.