Thirteen years after Fenerbahce became the first team to defeat Manchester United in a European game at Old Trafford, fellow Turkish side Besiktas ended their 23-match unbeaten home record in the Champions League.
Rodrigo Tello's first-half effort did the damage, just as Elvir Bolic broke Sir Alex Ferguson's team all those years ago - goalkeeper Rustu Recber the constant - with United left to do a spot of naval gazing over the winter months.
A point at Wolfsburg in a fortnight will still secure top spot in Group B, qualification having already been achieved.
But, Gabriel Obertan apart, Ferguson knows his United team laboured badly against a side that had collected just a single point from their four previous matches.
A bit like England manager Fabio Capello in Qatar, the United boss discovered his back-up is not really cutting it just now, leaving him to cross his fingers that the watching Rio Ferdinand heads a list of returning soldiers when battle recommences in February, when, unlike now, there will be no redemption after failure.
The outcome was particularly galling for Ben Foster, who had so little to do.
To say there was a bit of pressure on Foster before kick-off was sizeable understatement.
A lot of it was self-inflicted. In grumbling quite so publicly about his perceived status as Red Devils third choice goalkeeper while at the same time being good enough to start England's last two internationals, Foster ensured there would be a fairly intense focus on him the next time he was picked by Ferguson.
His recall was accompanied by words of high praise from his manager for CSKA Moscow stopper Igor Akinfeev, someone United are supposed to be considering as Edwin van der Sar's replacement when the veteran Dutchman eventually calls time on his stellar career.
Ferguson's assertion that rumours he wants to sign the Russia international are "not true" will be greeted with a pinch of salt by the sceptics and certainly Foster had no reason to feel comfortable.
So, to be beaten after 20 minutes by a long-range strike that appeared to catch him slightly flat-footed was not the best way for Foster to respond.
Consolation could be taken from the slack defending that created the space for Tello to shoot.
The strike itself took a slight deflection off Rafael Da Silva that took it further out of Foster's reach but it was with a slight shake of the head and a sense of foreboding that the former Watford goalkeeper picked the ball out of his goal.
United were fortunate not to be further behind at the break but Michael Fink spoiled an otherwise excellent central midfield display by clipping the outside of a post with a 12-yard effort after the home defence had been opened up far too easily once more.
Yet on the whole, it had been an encouraging first-half for a youthful Red Devils side that only needed to preserve that long unbeaten home run to confirm themselves as Group B winners with a game to spare.
Strikers Federico Macheda and Danny Welbeck both caused Besiktas problems in their own way.
The Italian was prepared to shoot from distance while Welbeck had a more nimble approach to unlocking the defence of a side that conceded eight to Liverpool on their last visit to England two years ago.
Obertan made the biggest impact.
For those still missing Cristiano Ronaldo, the Frenchman performed some fleet-footed stepovers and was not scared to use his pace down the right flank.
And, although his head seemed to drop near half-time when a couple of decisions went against him, it was Obertan who lifted flagging United spirits after an hour when he collected the ball inside his own half and sprinted past a couple of lame tackles before drawing an excellent low save out of Rustu.
He also looped a Macheda cross onto the roof of the net, at no little cost to Ibrahim Toraman, who was carried off with a suspected broken nose after accidentally being caught by an Obertan elbow.
But Obertan apart, a malaise had gripped home ranks. The introduction of Michael Owen was followed by a Ferguson expletive as he watched Darron Gibson curl a poor free-kick straight at Rustu.
It proved to be the Republic of Ireland international's last involvement as Michael Carrick and Patrice Evra were called upon to execute one of those famous rescue acts.
The task proved beyond them, with Rustu producing two excellent flying saves to deny Macheda and Wes Brown to give himself another night to remember at Old Trafford.Reuse content