Manchester United managed to come through a tricky clash with Real Sociedad courtesy of a 1-0 win in Spain, but it was not enough to see them top their group.
Having lost the reverse clash at Old Trafford by a scoreline of 1-0 courtesy of a dubious penalty awarded to the Spanish side when Lisandro Martinez was adjudged to have handled the ball, United needed to win by two clear goals to leapfrog the Spanish side on head-to-head, but they could only manage a 1-0 win.
This saw the two sides tied on head-to-head, and it reverted to goal difference, which even with a swing of 2 saw Sociedad squeeze through in top spot.
The result, which leaves Manchester United in second place despite accumulating joint second-most points in the competition, sees the Red Devils handed a further two games on top of an already hectic schedule in the New Year.
Worse yet, it will be against one of the Champions League sides that finished 3rd in their groups. It means that Erik ten Hag’s side will face one of:
FC Shakhtar Donetsk
There is plenty of potential for storylines in the clashes, whether it be a return to Old Trafford for now-Juventus midfielder Paul Pogba, Erik ten Hag’s return to Amsterdam or Cristiano Ronaldo return to Sporting Lisbon.
In fact, the Red Devils are slightly more likely to meet Juventus, Ajax or Bayer Leverkusen than any other side, as FIFA rules prevent two sides from the same nation being drawn against each other at this stage.
As a result, PSV cannot be drawn against Ajax, while Roma cannot play Juventus and Bayer Leverkusen cannot face Union Berlin.
The draw takes place on Monday the 7th of November.