Manchester United will take on Spanish club Real Sociedad in the Europa League last 16, while Tottenham face AZ Alkmaar and Rangers clash with José Mourinho’s Fenerbahce.
If United progress, they will meet either Romanian league leaders FCSB or French side Lyon in the quarter-finals.
Tottenham or Dutch club AZ Alkmaar will face the winner of Eintracht Frankfurt vs. Ajax in the last eight. Meanwhile, Rangers could play Roma or Athletic Bilbao if they overcome Fenerbahce.
The draw has placed Manchester United and Tottenham on opposite halves, meaning they could meet in the final in Bilbao.
The Europa League winner will secure automatic qualification for next season’s UEFA Champions League, adding extra stakes to the tournament.
With tough fixtures ahead, all three British clubs face challenging paths to the final.