Manchester United will face Spanish side Real Sociedad in the last 16 of the Europa League, while Tottenham will play AZ Alkmaar and Rangers meet Jose Mourinho’s Fenerbahce.
Should United advance, they will play Romanian league leaders FCSB or Lyon in the quarter-finals.
Spurs or Dutch side AZ Alkmaar will face Eintracht Frankfurt or Ajax in the last eight, while Rangers will meet Roma or Athletic Bilbao if they get past Turkish club Fenerbahce.
With Manchester United and Tottenham on opposite halves of the draw, they could – in theory – meet in the final in Bilbao, knowing the winner would get Champions League football next season.
Meanwhile, Chelsea will face FC Copenhagen in the last 16 of the Conference League.
United, Spurs and Rangers are all away in the first leg of their last-16 ties on Thursday, 6 March. The return legs take place on 13 March.
Chelsea will travel to Denmark for the first leg against Copenhagen on 6 March, with the return at Stamford Bridge seven days later.
