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.