This time, a Besiktas side that has offered little in the group managed to secure a shock 1-0 victory to inflict United's first home defeat in the group stages for eight years.
For a club that has reached the last two finals, the Red Devils seem to be doing their best to freewheel through this stage of the competition.
The irony won't be lost on Liverpool fans that, while their side have gone out, they battered Besiktas 8-0 at Anfield only two years ago.
United fans will argue this defeat did not matter a jot, except maybe prompt Sir Alex Ferguson to pick a slightly stronger line-up for the final tie in Wolfsburg in order to not surrender top place in the group.
But Ferguson's team have stuttered for form all season and could not cancel out Rodrigo Tello's 20th-minute winner despite a promising first-half display.
In the end, Patrice Evra should have won a penalty and Rustu Recber made two fabulous saves to thwart Federico Macheda and Wes Brown.
United's shadow side actually started brightly with Rustu fumbling a Park Ji-sung shot and Macheda being called offside from the rebound.
Nemanja Vidic was guilty of a poor header when left free from an Anderson corner and Macheda drilled wide after an impressive solo run.
With their first real attempt on target, Tello's speculative long-range shot deflected off Rafael, who was culpable in the build-up, and beat Ben Foster's dive.
It was a lesson that United, for all their possession, should perhaps heed an try their luck from distance more often and Michael Fink should have doubled the lead when clipping the outside of a post from a Bobo lay-off after a great move by the Turks.
The expected second half onslaught from the hosts never arrived although Park shot wastefully wide after a driving run by Darron Gibson.
Gabriel Obertan, probably the most impressive of the reserves handed an opportunity, forced a diving stop out of Rustu after one mazy dribble and then headed Macheda's cross onto the top of the goal.
Substitute Evra felt he should have had a penalty when he was clearly leaned into by Ibrahim Kas but the referee waved play on.
Owen then fed Anderson, whose cross really should have been converted by Macheda but Rustu tipped it over the top from close range. From the corner, Wes Brown beat his own keeper Foster to the ball but saw his header kept out by Rustu's spectacular save.
"Fortunately, we're through so it's good experience for them," said Ferguson.
"It's a penalty kick (with Evra). That's two games in a row in European football we've been denied stonewall penalties. It's not in the spirit of the game but what can you do about it?
"We just have to get on with it.
"We were a bit anxious - it's not a bad thing as they're young. It's expected they're going to make som mistakes. It's what you do when you're growing up, trying to learn the game.
"It was a solid performance - we just didn't get the goals we wanted.
"I think they've shown some really good things, which is encouraging for us, they just couldn't get the goals we needed."
United at least have the chance to redeem themselves in Wolfsburg but the fact of the matter is they are through without ever looking convincing at all in this season's competition.
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I am a turkish,and I like Besiktas,because,this team have a mysterious soul,and our supporter is very love this team,Rustu Recber is so good keeper.....
By alican.. Posted November 26 2009 at 8:45 AM.