Manchester United's 23-match unbeaten streak at home in the Champions League came to an end as they went down 1-0 to Besiktas at Old Trafford.
United, who only needed one point to win Group B with one match remaining, fell victim to a long-range bullet from Rodrigo Tello as the Turkish champions snapped their seven-year away losing run in the competition.
Last season's runners-up must now win away to Wolfsburg on December 8 if they are to top Group B while Besiktas narrowly kept alive their hopes of earning a Europa League berth ahead of CSKA Moscow.
United made a blistering start to the match, swamping the Besiktas defence and enjoying a host of gilt-edged chances.
Rafael found Gabriel Obertan within two minutes of the start, the Frenchman squaring a great chance to Federico Macheda, who just failed to get a touch.
Nemanja Vidic also missed a sitter, his header from an Anderson corner somehow spinning off at a right-angle to the goal despite the Serb having done all the hard work in losing Matteo Ferrari towards the right post.
Macheda came closest for United, in the 19th minute, when he received the ball on the right wing before cutting back inside with a swagger and drilling a low shot just past the right post.
But it was Besiktas who made the most of their opportunities, with Tello unleashing a bullet of a shot after being allowed space and time in midfield.
The ball took a slight deflection off the shoulder of a back-tracking Rafael, just enough to wrong-foot Ben Foster, before curling into the back of the net on the left side of goal.
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