United tonight tumbled out of the Champions League after a 2-1 defeat to Benfica.

As well as the prestige involved, and the chance to challenge for the trophy they won in 1999, an early exit means United missing out on up to £15million in earnings.

There was not even the consolation of a UEFA Cup place, as United finished bottom of Group D.

Here, we look at 10 of their worst defeats.

1952 - FA Cup third round v Hull City (h), lost 0-2

It should have been no contest. Matt Busby's soon-to-be-champions taking on a team who would finish 18th in the Second Division. One of the greatest days in Hull history.

1955 - Division One v Manchester City (h), lost 0-5

Defeat to your neighbours is never welcome. By this margin, at Old Trafford, was approaching criminal. Goals from Johnny Hart, Paddy Fagan (2) and Joe Hayes (2) crushed the `Busby Babes'.

1974 - Division One v Manchester City (h), lost 0-1.

The day United fell out of the First Division. Results elsewhere had already condemned the club to relegation but Denis Law's famous back heel has gone down in City folklore as the moment their rivals went down.

1980 - Division One v Ipswich Town (a), lost 0-6 (2nd).

Ripped apart by Ipswich's Dutch duo Arnold Muhren and Frans Thijssen, United would have suffered even greater humiliation had Gary Bailey not saved three penalties - one twice taken.

1984 - FA Cup third round v Bournemouth (a), lost 0-2 (4th).

The holders fell at the first hurdle to the south coast Third Division club. It was a result which led to calls for manager Ron Atkinson's head, although Mr Bojangles clung onto his job.

1989 - Division One v Manchester City (a), lost 1-5 (13th).

The defeat which is etched onto Sir Alex Ferguson's mind more than any other. The Scot had struggled to impose his authority on the club and this humbling reverse suggested they were as far away as ever.

1994 - Champions League v Barcelona (a), lost 0-4 (2nd).

Ferguson juggled with his overseas players and dropped Peter Schmeichel. Romario ran riot on a sorry evening in the Nou Camp.

1995 - Football League Cup 2nd round v York City (h), lost 0-3.

Paul Barnes struck either side of half-time before Tony Barras wrapped up an unlikely away win for the Third Division side against a United line-up including Gary Pallister, David Beckham, Lee Sharpe and Ryan Giggs.

2002 - Champions League qualifier v Zalaegerszegi (a), lost 0-1

The Hungarians had never qualified for Europe before this season and were expected to be swept away having switched the first leg tie to Budapest. Bela Koplarovics' last-minute goal sparked celebrations which lasted a fortnight - until United set the record straight by winning the second leg 5-0 at Old Trafford.

2005 - Champions League Group D v Benfica (a), lost 2-1

Despite scoring just two goals and obtaining six points from their opening five group games, United went to Benfica knowing they would reach the last 16 with a victory. All was going to plan when Paul Scholes scrambled an opening goal, but Benfica hit back to win 2-1 with goals from Geovanni and Beto and United were out of Europe.

What now for United? Have your say.