Basel: Manchester United crashed out of the Champions League at the group phase for only the third time in 16 years following a stunning 2-1 loss at Swiss champions Basel on Wednesday. (Agencies)
Six years to the day since they last bade farewell at the group stage, following a 2-1 loss at Benfica, last year's beaten finalists were undone by goals in each half from Marco Streller and Alexander Frei.
Despite needing just a point to go through from Group C, Sir Alex Ferguson's side fell to their first away defeat in the group phase in five years, but not before Phil Jones' late goal had given them a vain glimmer of hope.
Victory allowed Basel to book their place in the last 16 for the first time since 2002-03, while for United, who had reached three of the last four finals, there is the unwelcome consolation of the Europa League.
The last time United wore white against a team sporting maroon and blue in European competition was in May's Champions League final defeat by Barcelona, but few can have predicted Wednesday's game would end with similar heartache.
Contrary to expectation, Ferguson chose to field Wayne Rooney as a lone striker and left Danny Welbeck on the bench, despite the absences through injury of both Javier Hernandez and Dimitar Berbatov.
Goalkeeper David de Gea also returned after being rested for the 1-0 win at Aston Villa, but his first contribution was an unconvincing punch and his second presented Basel with the opening goal.
A clash of heads between United defenders Nemanja Vidic and Chris Smalling left the latter on the turf, but play continued and when de Gea could only partially clear Xherdan Shaqiri's cross, Streller pounced to half-volley home.
United had started assertively but the goal cowed them and there were 20 aimless minutes until they fashioned a real chance, with Rooney and then Park Ji-Sung both unable to convert Nani's low cross from close range.
Rooney then shot straight at Yann Sommer from Ryan Giggs' intelligent reverse pass, before the 22-year-old goalkeeper saved bravely at the feet of Nani.
The visitors were building up a head of steam but shortly before half-time they received another setback when captain Vidic had to be stretchered off after his knee appeared to buckle in a challenge with Streller.
There was renewed purpose to the away side's play in the second half, however, and Rooney went close to an equaliser when he curled narrowly wide following another astute through-ball by Giggs.
Shaqiri gave a reminder of Basel's threat at the other end when he clipped a shot narrowly wide from the edge of the box and moments later de Gea had to produce a superb finger-tip save to keep out Frei's free-kick.
United roared back though and Marcus Steinhofer almost scored a famous own goal when he volleyed an attempted clearance against his own crossbar.
As the half wore on, Basel found it harder and harder to get out of their own half, with Rooney dragging wide after cutting in from the left and then bending the ball a couple of feet wide of the right-hand post.
The goal would not come, however, and with six minutes remaining, Frei dived to head home a cross from the excellent Shaqiri to send St Jakob-Park into raptures.
Jones scrambled in a consolation amid the game's dying embers, but it was too late to avert one of the most painful losses of the Ferguson era.
Basel: Manchester United crashed out of the Champions League at the group phase for only the third time in 16 years following a stunning 2-1 loss at Swiss champions Basel on Wednesday.