Manchester United endured a difficult night in Germany as RB Leipzig claimed a 3-2 victory and sent the Reds out of the Champions League.
The hosts, who needed to win to qualify for the knock-out stages, took a very early lead on two minutes through danger-man Angelino, who fired home at the back post.
Amadou Haidara added a second, on the volley, 11 minutes later and Leipzig had further chances to increase the advantage, including a disallowed goal by VAR for a clear offside.
After Bruno Fernandes hit the bar with a brilliant free-kick on 68 minutes, the home team claimed a third when a deflected cross was allowed to travel all the way through to substitute Justin Kluivert to compound United's frustration.
Fernandes pulled a goal back from the penalty spot, before substitute Paul Pogba rose to meet a corner, with the ball deflecting in off Maguire and then Ibrahima Konate to make it 3-2, but it was sadly too little, too late for the Reds.
FIRST HALF - TOUGH GOING IN GERMANY
Ole made five changes to the side that came back – again – to win at West Ham at the weekend. David De Gea, rested as a precaution for the Hammers clash, returned between the posts, while Luke Shaw, fit again after a hamstring injury, lined up in a five-man defence. In front of them, Nemanja Matic, Bruno Fernandes and Marcus Rashford were all back in the starting XI, with Anthony Martial and Edinson Cavani missing through injury, and Fred suspended.
United knew before kick-off that a draw would be enough to see us through to the last 16, but the Reds got off to the worst possible start when Angelino put the hosts in front on two minutes. A curling ball from Leipzig skipper Marcel Sabitzer, across the United defence, went all the way through to the no.3, whose left-foot drive found the bottom corner.
Ole’s men looked to fashion an immediate riposte and went close on nine minutes through Greenwood. He could have passed to Rashford, but opted to cut inside onto his left foot and his shot was easily collected by Peter Gulacsi.
On 13 minutes, proceedings got worse for the Reds when opening scorer when Angelino sent a wicked ball to the back post, where the unmarked Haidara crashed home a volley.
How Emil Forsberg put his shot wide went Angelino found him free in the area, eight yards out, only he will know, while United breathed another sigh of relief on the half-hour when Willi Orban’s finish was ruled out by VAR. The Leipzig defender was clearly offside when Ibrahima Konate’s header bounced off the post and into Orban’s path to tap home, but the goal was ruled out, thankfully.
Rashford saw an effort blocked soon after as the Reds looked to regroup at the break.
SECOND HALF – REDS SO CLOSE
Donny van de Beek entered the fray for the second period, in place of Alex Telles, and he got United into the box twice in quick succession during the opening exchanges of the half.
A dangerous Fernandes free-kick flashed across the face of goal on 55 minutes but no United player could get a touch on it, as Scott McTominay and Harry Maguire looked to pounce. Fernandes saw a dipping effort pushed just wide on 66 minutes, before the Portuguese ace struck the crossbar with a superb free-kick.
United were pushing for a way back into the game, but, three minutes later, things got even better for the hosts when a deflected Angelino cross found its way through to Kluivert to simply tap past David De Gea.
Hope looked all but lost for the Reds who peppered Gulacsi’s goal thereafter. We were given a lifeline via a penalty on 80 minutes, when Greenwood was pushed over by Konate. Fernandes duly converted and, two minutes, later a combination of Pogba, Maguire, Konate and Gulacsi touches saw the ball end up in the net from a corner.
United threw everything at Leipzig and Pogba's dangerous cross was almost turned into his own net by Nordi Mukiele, only for it to fly into the foot of Gulacsi instead.
The Reds now have to settle for the last 32 of the Europa League instead, with the Manchester derby on Saturday next on the agenda.
Team line-ups
RB Leipzig: Gulacsi; Mukiele, Konate, Orban, Angelino (Halstenberg 87); Sabitzer (c), Haidara, Kampl (Adams 75); Nkunku, Forsberg (Y. Poulsen 56); Olmo (Kluivert 56).
Subs not used: Tschauner, Martinez, Sorloth, Martel, Wosz.
Goals: Angelino 2, Haidara 13, Kluivert 69
Booked: Mukiele, Sabitzer, Kluivert, Adams.
United: De Gea; Wan-Bissaka (Fosu-Mensah 78), Lindelof (Tuanzebe 78), Maguire (c), Shaw (Williams 61), Telles (van de Beek 46); Matic (Pogba 61), McTominay, Fernandes; Rashford, Greenwood.
Subs not used: Henderson, Grant, Bailly, James, Lingard, Mata, Ighalo.
Goals: Fernandes 80 (pen), Pogba 82
Booked: Fernandes, Shaw, Williams, Lindelof.