Manchester United crashed out of the Champions League and had the safety net of the UEFA Cup ripped away as well on a miserable night at the Stadium of Light.
Sir Alex Ferguson may have found it easy to fend off talk about his long-term future at Old Trafford in the build-up to the clash with Benfica.
But those questions are certain to come again, and with added venom after a defeat which costs Malcolm Glazer up to £15million in prize-money and leaves United with no European combat to look forward to after the New Year for the first time in a decade.
The outcome was all the more galling as Villarreal's defeat of Lille meant only a draw was required.
But once Geovanni and Beto had turned the game on its head by replying to Paul Scholes' early opener, there was no way back.
There could hardly have been a more poigniant fixture to mark United's European return since the death of George Best.
It was against Benfica that Best won the European Cup in 1968 and on the ground upon which the Portuguese giant's current stadium is built where he enjoyed his finest hour and a half, the stunning 5-1 triumph two years earlier.
Best ignored the tactical strategy of Matt Busby by blitzing Benfica from the start that night, and the modern-day Red Devils began in equally storming form this evening, netting within six minutes.
After seeing Scholes break his 22-game scoring duck against Portsmouth at the weekend, Ferguson suggested his influential midfielder might go on a run. And the Scot's words were proved accurate when Scholes arrived unmarked at the far post to meet Gary Neville's cross.
The scrambled finish may not have been very convincing, but the goal - his first in Europe since March 2004 - appeared so precious and for a time it looked like United would overwhelm their understrength opponents, who were lacking five key men, including the Liverpool target Simao Sabrosa.
But, after Cristiano Ronaldo in particular wasted possession on his return to Portugal, United were undone in unexpected fashion when Nelson found space on the right and drove a low cross to the edge of the six-yard box.
There appeared little danger until Neville was caught on his heels, failing to track Geovanni, who launched himself at the ball and sent a firm diving header flying into the net.
It took a while for United to clear their heads and Ronaldo, having already been booked, risked becoming the third Red Devil to be sent off in the Champions League by continually questioning the decisions of referee Kyros Vassaras, who thankfully proved to be a patient man.
Scholes had a long-range effort tipped over by Quim and Wayne Rooney failed to connect with Ronaldo's low, near-post cross before the visitors, whose confidence appeared so high in the build-up, were sent spinning to the floor by Beto.
The Brazilian wasted no time in unleashing a fierce 25-yard drive when Alan Smith's clearing header landed perfectly at his feet. Edwin van der Sar might have had the shot covered but a flick off Scholes on its way through a packed penalty area gave the Dutch goalkeeper no chance of saving.
United responded in typically beligerent fashion, knowing they were vulnerable on the counter attack.
The pattern continued after the re-start and Ronaldo's unhappy night did not get any better when Scholes and the ineffective Ruud van Nistelrooy combined to set up a glorious shooting chance which the winger dribbled harmlessly wide of the far post.
It was no surprise when Louis Saha was called off the bench after an hour but in switching Rooney to the left wing berth as Giggs went off, Ferguson was providing more ammunition to the critics who have waited so long to shoot him down.
No matter where he was supposed to be stationed, Rooney was determined to drag United out of their crisis but when he floated a free-kick wide just after the hour mark, he feared the worst.
If word had filtered through to the United bench of Villarreal taking the lead in Spain, meaning Ferguson's side only needed a draw to go through, it could only have increased the desperation in the visiting ranks.
Yet, in going for broke they left themselves open at the back.
Joao Pereira blasted into the side-netting, Geovanni drove straight at Van der Sar.
Ferguson implored his team to push forward and the four minutes of injury time brought more hope. But the days of those marvellous United fightbacks appear to be finished and it is bound to be asked whether Ferguson is too.
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