A young Manchester United side were beaten 2-1 by Astana in -15C temperatures in Kazakhstan.
Having already qualified for the knockout stages, manager Ole Gunnar Solskjaer opted for youth with three debutants and seven teenagers in his starting line up.
Captaining the side for the first time, Jesse Lingard ended a 10-month wait for a goal, giving United the lead after ten minutes with a low drive into the bottom corner.
Dmitriy Shomko pulled Astana level 10 minutes after the restart before debutant Di'Shon Bernard scored an own goal to give the home side the lead.
Astana goalkeeper Nenad Eric made two incredible saves within a minute of each other as the hosts held on for their first points of the competition.
Having already qualified for the last 32, teenagers Ethan Laird, Bernard and Dylan Levitt were handed their debuts, while 36-year-old goalkeeper Lee Grant was given his first start of the season.
Mason Greenwood had the first real chance of the match after Lingard’s through ball, as the striker's drive was palmed away by goalkeeper Nenad Eric at the near post.
Lingard gave United the lead after just 10 minutes, ending a run of 28 games without a goal in the process. The 26-year-old picked up the ball on the edge of the area and smashed a low drive into the bottom corner.
The United skipper almost doubled their lead with an effort from 25-yards out, but his left footed effort was just wide of the post.
The home side should have been level after Luke Shaw was caught napping and allowed Abzal Beysebekov's pass through to Dorin Rotariu at the back post, but he pulled his effort wide with just Grant to beat.
Lingard tried his luck from distance once again, this time it took a deflection off Evgeny Postnikov and looped onto the roof of the net, with Eric was beaten.
Astana started the second half brightly with Postnikov heading over from Runar Mar Sigurjonsson cross at the back post, before United defender Bernard slid in to intercept Rotariu's ball in and almost turned it into his own net as it looped over.
Postnikov then got up well to meet Rotariu's free-kick, but his header was straight at Grant who made the save comfortably.
Astana continued to push for an equaliser as Ivan Maevski was next to miss the target in a great position. United failed to clear a cross into the box and Maevski had two bites at it, dragging the second wide.
Tahith Chong should have made it 2-0 but missed an absolute sitter. From just four yards out, he managed to chip the ball over the crossbar with an open goal looming.
He was made to pay for that miss immediately as the hosts went straight down the other end and levelled.
It was the first goal United have conceded in the Europa League this season and it was brilliantly taken by Shomko as he took the ball down in the area and drilled it into the bottom corner.
Six minutes later and the home side were in front. Bernard, who almost scored an own goal a few minutes before, gifted Astana the lead.
Again he came sliding into to cut out the cross but this time turned it past Grant and into his own net.
Astana should have put the game to bed with just under 20 minutes to go but Sigurjonsson fired wide from Rotariu cross after a quick counter.
Angel Gomes almost got United back on level terms with a free-kick that the midfielder won himself. From the edge of the box, Gomes curled it over the wall and it was heading into the top corner, but he was denied by a wonderful diving save from Eric.
Eric made another flying stop just a minute later this time denying Greenwood from Gomes’ cross into the penalty area, as United were left to rue their missed opportunities.
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