Manchester were dumped out of the Champions League after going down 3-2 against RB Leipzig.
United got off to the worst possible start in Germany, where the five-man backline was caught napping just two minutes in.
A sweeping ball from Leipzig skipper Marcel Sabitzer found Angelino and the left-back, on loan from Manchester City, rifled a low shot past De Gea.
Angelino found Amadou Haidara ghosting in at the far post to fire home a second for Leipzig.
Bruno Fernandes saw a brilliant, dipping free-kick hit the bar from 20 yards in the 68th minute - but a minute later United's hopes were all but over.
Harry Maguire and David De Gea hesitated as a bobbling Angelino cross came over, with Leipzig substitute Justin Kluivert reacting quickly and clipping the ball over United's goalkeeper.
Fernandes pulled one back from the penalty spot, before Paul Pogba climbed off the bench to head home and ensure a nervy finish.
Here's how they rated:
Man Utd (3-4-1-2)
De Gea 4
Little chance of stopping first two goals. At fault for Leipzig's third after maguire mix-up.
Lindelof 4
Poor positioning throughout the game and defensively suspect again.
Maguire 3
Vocal but woeful. Mix-up with De Gea led to Leipzig's third goal. Booked.
Shaw 4
Returned after a month out for his 150 th United game but off the pace. Subbed.
Wan-Bissaka 2
Afforded Angelino too much space throughout the game. Defensively naïve.
Matic 4
Tidy enough on the ball but did not do enough with it. Subbed for Pogba.
McTominay 5
Put Rashford through on goal just before half-time. Committed and diligent.
Telles 4
Failed to keep tabs on Haidara, allowing him to plunder Leipzig's second. Subbed.
Fernandes 6
Hit the bar with free-kick and slotted home penalty.
Rashford 4
Put through on goal just before the break but fluffed the chance to score.
Greenwood 5
Wasted an early chance to level for United. Headed over from a Telles corner.
Subs: Van de Beek 6 (Telles, 45), Pogba 6 (Matic, 61), Williams 5 (Shaw, 61)
