Manchester United stumbled into the last 16 of the Europa League after losing 2-1 at home to Ajax on a night when Ryan Giggs had to wait for his 900th appearance for the club.
Javier Hernandez's early goal appeared set to hand the Red Devils a comfortable evening as he put his team 3-0 up on aggregate, but Ajax hit back through Aras Ozbiliz and Toby Alderweireld to become the first Dutch team to record a victory at Old Trafford.
United were in front after just six minutes when Park Ji-sung intercepted the ball and fed Dimitar Berbatov, who picked out Hernandez in space and the Mexican striker turned back inside before beating Kenneth Vermeer with a composed finish.
Ajax got themselves back in the contest before half-time when Ozbiliz's deflected shot from the edge of the area flashed past David de Gea, although there was a suspicion of handball in the build-up.
The visitors continued to press for further goals in the second half and De Gea produced a wonderful one-handed reaction save to turn Siem de Jong's header from a corner over the bar.
The woodwork came to Ajax's rescue at the opposite end as a quick break from United resulted in Nani cutting inside on his left foot before crashing a shot against the bar.
Alderweireld headed home Ozbiliz's free-kick with three minutes to go to set up a nervy finale, but United hung on to set up a last-16 meeting with Athletic Bilabo, who beat Lokomotiv Moscow on away goals.
In his programme notes, Sir Alex Ferguson had dismissed the theory this was a competition his team did not want to be involved in.
However, he will know significant improvement will be required against an Athletic outfit that have already secured a Copa del Rey final meeting with Barcelona and are pushing strongly for a place in next season's Champions League.
Memories
Memories of the manner in which his side tossed away a two-goal lead in the Champions League against Basel before eventually scraping a draw that ultimately cost them their place in the competition burned deep enough in Ferguson's psyche for the United boss to issue a warning on Wednesday.
United started as though the prospect was unthinkable. Nani had already forced Vermeer into a flying save when Berbatov brilliantly found Hernandez with a defence-splitting pass.
The Mexican skipped inside Jan Vertonghen before finding the bottom corner.
It was the fourth consecutive game Hernandez has scored, taking his season's tally to 10 and confirming he has now found the form which made him one of last season's sensations.
Had Hernandez been more selfish when he was set free by Fabio not long afterwards, United might well have doubled their lead.
As it was, he opted to try and pick out Berbatov with a square ball which Vertonghen was wise to.
It was not the last time the Ajax skipper made a timely intervention, which must have been noted by both Harry Redknapp and Stuart Pearce, who were present in the directors' box.
And the visitors' other star man, Christian Eriksen, took his cue to start making an impact at the other end.
De Gea was unconvincing as he pushed one of Eriksen's teasing crosses out of his six-yard area and was fortunate Rafael was on hand to complete the clearance.
The large and voluble visiting contingent drew boos from their home counterparts as they launched into a song in favour of former hero Luis Suarez.
It was not long before they had something more meaningful to agitate United with though as the home defence failed to smother growing danger outside their penalty area.
Phil Jones' intervention only presented Ozbiliz with a half-volley which he lashed home in clinical fashion with the aid of a deflection.
Jones had been at the centre of a pre-game stir when the official UEFA team sheet had indicated he was about to become United's youngest captain. When the teams emerged though, Park Ji-sung was wearing the armband and his 20-year-old team-mate relegated to a mere foot soldier.
It is surely a job Jones will get one day though and his timely second-half clearance came during a period of the game when Ajax were starting to get on top.
Nicolas Lodeiro wasted a good opportunity which Eriksen had created, then De Jong powered a header goalwards that brought a brilliant reaction save from De Gea.
Ferguson was sufficiently vexed to bring on Paul Scholes in a double change that highlighted Jones' versatility as he moved into central midfield alongside the old maestro.
The move worked to the extent of halting Ajax's incessant stream of attacks but it was not until Danny Welbeck made his way on to the pitch that Nani flickered back into life, cutting in from the right flank before clipping the bar with a brutal shot.
Alderweireld's late header really made life interesting but whilst it gave Ajax a victory they just about deserved on the night, it was not enough.