Manchester United crashed out of the Champions League as they lost to Benfica in Lisbon's Stadium of Light.
Paul Scholes gave United the perfect start in their quest to reach the knockout stage with a close-range finish after only six minutes.
But Geovanni's diving header quickly put Benfica level and Beto fired in a second from 20 yards before half-time.
The defeat leaves Sir Alex Ferguson's side bottom of Group D and means they do not even qualify for the Uefa Cup.
Ferguson cut a disconsolate figure sitting back in his dug-out at the final whistle and is now poised to face even more hard questions about his Old Trafford future.
And it was the first time United have failed to emerge safely from the group stages of Europe's elite competition for 11 years.
United arrived in Lisbon hoping to deliver a performance to celebrate the memory of the late George Best, who rose to world fame in this legendary Lisbon arena.
Instead they delivered another miserable Champions League show that betrayed their proud European heritage.
Ferguson signalled his intentions with an attacking line-up - using Cristiano Ronaldo and Ryan Giggs on the flanks and Wayne Rooney and Ruud van Nistelrooy up front.
And it was another attack-minded player, Scholes, who gave them a dream start after six minutes.
Giggs released Gary Neville down the right flank, and he delivered the perfect cross for Scholes to bundle a finish past Quim from six yards.
But United, instead of building on the lead, were suddenly careless in possession and conceded the initiative to Benfica.
And they paid the price after 16 minutes when Nelson's perfect cross set up Geovanni for a diving header that gave Edwin van der Sar no chance.
Ronaldo was having a miserable return to Portugal, where he was a target for constant taunts because of his links with Benfica's great rivals Sporting Lisbon.
And the youngster's frustration showed when he was booked for a petulant kick at Beto.
Beto (centre) scored Benfica's winner
United's attacking threat was almost non-existent, but Scholes nearly lifted the spirits again with a long-range drive that was turned over the top by Quim.
Benfica, in contrast, were rampant and it was no surprise when they plunged United's hopes of staying in the competition into further doubt with a second goal after 34 minutes.
Alan Smith's defensive header fell to Beto, and the Brazilian flashed a fierce drive past Van der Sar with the help of a deflection off Scholes.
United's best move of the game almost produced the equaliser after 57 minutes, when Scholes and Van Nistelrooy linked and set up Ronaldo, but he pulled a tame finish across the face of goal.
Ferguson gambled with two substitutions in quick succession, replacing Giggs with Louis Saha and sending on Park Ji-Sung for Ronaldo.
And as United pressed forward, Benfica almost punished them on the counter-attack as substitute Joao Pereira shot wastefully into the side-netting with only Van der Sar to beat.
Benfica: Quim, Alcides, Luisao, Anderson, Leo (Ricardo Rocha 90), Nuno Assis (Joao Pereira 73), Petit, Beto, Nelson, Nuno Gomes, Geovanni (Mantorras 80).
Subs Not Used: Nereu, Bruno Aguiar, Dos Santos, Roque.
Booked: Beto, Geovanni, Petit.
Goals: Geovanni 16, Beto 34.
Man Utd: Van der Sar, Neville, Ferdinand, Silvestre, O'Shea (Richardson 87), Ronaldo (Park 67), Smith, Scholes, Giggs (Saha 60), Rooney, van Nistelrooy.
Subs Not Used: Howard, Brown, Fletcher, Bardsley.
Booked: Ronaldo, Neville, Ferdinand.
Goals: Scholes 6.
Ref: Kyros Vassaras (Greece).