They may have produced a more entertaining display than in recent weeks, yet Manchester United's 3-2 defeat at the hands of Wolfsburg in Germany last night saw Louis van Gaal's side knocked out of the Champions League at the group stage.

The Red Devils opened up their campaign with a 2-1 loss away at PSV Eindhoven, although they looked to be on course for qualification when seven points were picked up from the home clash against Wolfsburg and a double-header with CSKA Moscow.

A 0-0 home draw with PSV Eindhoven on matchday five proved to be the defining moment, given that it left United needing to win in the Volkswagen Arena to secure their place in the knockout stages.

It is the fourth occasion that United have failed to progress beyond the group phase and here, Sports Mole takes a look at how each of their seasons fared following those early exits.

1994-95

This was the first season in which the group stage had been introduced to the Champions League and it is fair to say that United were dealt a tough draw, with Barcelona and Galatasaray both included. The 4-0 demolition at Camp Nou is what most people remember, yet it was the 3-1 defeat away in Gothenburg - inspired by future United winger Jesper Blomqvist - that proved costly.

Free from European commitments, United embarked on a battle for the Premier League title with Kenny Dalglish's Blackburn Rovers. But, while Rovers had their talisman - Alan Shearer - in clinical mood, United's best player Eric Cantona was serving a lengthy ban for his infamous kung-fu kick at Selhurst Park in January 1995.

The Red Devils still pushed Dalglish's charges all the way and they actually would have won the title if they could have recorded a victory against West Ham United at Upton Park on the final day, but a number of wasted chances resulted in a 1-1 draw. Things did not improve a week later either when Paul Rideout's goal was enough for Everton to beat United in the FA Cup final at Wembley.

Premier League: Second
FA Cup: Runners-up
League Cup: Third round

2005-06

Grouped with Villarreal, Benfica and Lille, it was almost unthinkable that United would not advance through to the knockout stages. However, having scored just three goals in six games - winning only once - they finished bottom of the pile.

Despite finishing second in the Premier League, they never really looked like winning the title. Just as they had been the season before, Jose Mourinho's Chelsea were the strongest team in England by a distance. United were also unable to go deep in the FA Cup, losing 1-0 at Anfield in a game best remembered for the horrific leg injury sustained by Alan Smith.

There was at least some joy in the form of the League Cup, though. After overcoming Blackburn Rovers in a tight two-legged semi-final, United waltzed to glory thanks to a 4-0 win over Wigan Athletic in the final. It was a match that marked the beginning of the end of Ruud van Nistelrooy's time with the club. The Dutchman was left on the bench for the game and departed for Real Madrid at the end of the campaign.

Premier League: Second
FA Cup: Fifth round
League Cup: Winners

2011-12

United lost just once in a group that also contained Benfica, Otelul Galati and Basel. Nevertheless, it was a defeat that proved fatal to their chances of progression. A win or a draw away in Basel on matchday six would have secured progression, but United contrived to lose 2-1, meaning that the hosting Swiss side advanced at their expense along with Benfica.

It set the tone for what was a truly miserable season for those of a United persuasion. Having traded blows with neighbours Manchester City during the run-in, the destination of the title went down to the last day. When the final whistle was blown at the Stadium of Light, a 1-0 win for Ferguson's men was enough to crown them champions. But, Man City were still playing against Queens Park Rangers at the Etihad Stadium and when the ball broke for their frontman Sergio Aguero, he scored the most dramatic of stoppage-time winners to wrestle the trophy out of United's clutches.

Early exits were also suffered in both of the domestic cups, while finishing third in their Champions League group meant that United were permitted to play in the Europa League after Christmas. Javier Hernandez scored twice in a 3-2 aggregate win over Ajax, but eventual finalists Athletic Bilbao were too strong in the last 16.

Premier League: Second
FA Cup: Fourth round
League Cup: Fifth round
Europa League: Round of 16