Manchester United will take on Spanish side Real Sociedad in the Europa League last 16, while Tottenham have been paired with Dutch club AZ Alkmaar.
Rangers, meanwhile, will face Jose Mourinho's Fenerbahce in a tough knockout clash.
Should United progress, they will meet either Romanian league leaders FCSB or French side Lyon in the quarter-finals.
Spurs or AZ Alkmaar will face the winner of Ajax versus Eintracht Frankfurt, while Rangers will go up against either Roma or Athletic Bilbao if they advance past Fenerbahce.
