Manchester United will face French side Saint-Etienne in the Europa League last thirty-two, while Tottenham Hotspur meet Belgian team Gent.
United midfielder Paul Pogba is set to face older brother Florentin, who plays for the eighth-placed Ligue 1 side.
Spurs have never met Gent, who finished third in the Belgian top-flight last season, in a competitive fixture.
United’s first leg will be played on Wednesday, fifteen February, while Spurs play the following day.
The Europa League final will be held at Stockholm’s Friends Arena on twenty-four May.