Manchester United crashed out of the Champions League after falling just short of a remarkable comeback at RB Leipzig as Ole Gunnar Solskjaer's side lost 3-2 in Germany.
Having started Group H with a win over last season's runners-up Paris Saint-Germain and a five-star display at home to Tuesday's opponents, the Red Devils undid that fine work and have now dropped into the Europa League.
United only required a point from their final two matches to reach the knockout phase.
But last week's loss to PSG was compounded by a heartbreaking defeat at Leipzig as poor defending proved too much to overturn in a grandstand finish.
Angelino, on loan from Manchester City, had Julian Nagelsmann's men off to a dream start by lashing home inside two minutes, with Amadou Haidara adding a second soon after.
United could easily have fallen further behind before substitute Justin Kluivert took advantage of hesitant defending to put Leipzig three goals ahead, moments after a Bruno Fernandes free kick hit the bar in the second half.
It proved a hole too big for Solskjaer's comeback kings to dig themselves out of, despite Fernandes scoring from the spot and substitute Paul Pogba heading in off the back of Harry Maguire in the final 10 minutes.
Meanwhile, Chelsea's Jorginho converted a penalty as a much-changed side were held to a 1-1 draw by Russians Krasnodar at Stamford Bridge on Tuesday in their final Champions League Group E game with nothing at stake.
Frank Lampard's side had already secured top spot and Krasnodar the Europa League qualifying place by finishing third.
But the match was still played at a breezy tempo in front of 2,000 fans as the hosts made 10 changes to their line-up.
Krasnodar took the lead when midfielder Remy Cabella finished a fine move by firing low into the bottom corner in the 24th minute.
It was only the second goal conceded by Chelsea in the competition this season, but the lead lasted only four minutes.
Chelsea forward Tammy Abraham was upended in the box and Jorginho, who missed a spot kick in the corresponding fixture in Russia in October, made no mistake this time.
Abraham forced an excellent save from Krasnodar goalkeeper Yevgeni Gorodov in the second half and might have done better with a header when teed up by N'Golo Kante on what was ultimately a frustrating night for the England striker.
In the other Group E match, Jules Kounde's excellent volley from the edge of the box and Youssef En Nesyri's double sealed a 3-1 win for section runners-up Sevilla at Stade Rennes, who grabbed a consolation through Georginio Rutter's late penalty.