Manchester United's bid for a tenth consecutive appearance in the knockout stages of the Champions League was shattered by a 2-1 defeat at the hands of Benfica.
First-half goals from Brazilian striker Geovanni and midfielder Beto put the Portuguese champions into the last 16 after Paul Scholes had given United a 6th-minute lead.
Villarreal's victory over Lille in the other group D match meant a draw would have been enough to put Sir Alex Ferguson's side through.
But the equaliser they sought throughout a tense second half never seriously looked like coming against a Benfica side that, missing five first-team regulars, stuck to their cautious game plan with steely resolve.
At the start of the night, United knew only a win would be enough to assure them of progress and Ferguson appeared determined that if his side were to go out it would be with a bang rather than a whimper, starting with both Cristiano Ronaldo and Ryan Giggs on the wings.
It was to be United who landed the first telling blow, thanks to Benfica's back four assuming that Gary Neville, overlapping down the right touchline, had strayed into an offside position.
The whistle never came and the England fullback duly squared the ball into the goalmouth, where an unmarked Scholes, scarcely able to believe his luck, bundled it over the line.
The yellow card Ronaldo had been flirting with finally arrived in the 23rd minute after a late lunge at Beto, but his indiscipline did not prevent United from gradually asserting control of the match.
A sustained period of pressure culminated in a 25-yard drive from Scholes being tipped over Benfica goalkeeper Quim, and the English side's back four appeared to be coping, albeit only just, with the rapid counter-attacking of their hosts.
But there was little they could do about Benfica's second goal. Picking up a loose ball 30 yards out, Beto let fly with a highly speculative effort that paid a huge dividend thanks to a deflection off Scholes which left van der Sar helpless.
Two minutes later Mikael Silvestre was extremely fortunate not to concede a penalty after being outpaced by Geovanni and tangling with him just inside the area. Both men went to ground and the Greek referee, Kyros Vassaras, gave Silvestre the benefit of the doubt, awarding the free-kick to United.
Benfica had a similar let-off ten minutes after the restart when Ronaldo, teed up by van Nistelrooy 15 yards out, shanked his shot across the goalmouth.
Minutes later, Ryan Giggs made way for Louis Saha, with Ronaldo following him off shortly afterwards to allow Park Ji-Sung to enter the fray.
The changes lifted United's tempo but failed to sharpen their cutting edge.
Benfica's breaks always looked the most likely source of a further goal and substitute Joao Pereira, set up by Nuno Gomes, could have killed the game with 15 minutes left, his shot ending in the side netting.
