Manchester United failed to qualify from a group most pundits expected to be easy and straightforward. PSV, Wolfsburg and CSKA Moscow was a combination that any English team would have been happy with.
However, after a 3-2 defeat to Wolfsburg, United could only qualify for the Europa League. Given the tournament's reputation among many supporters, this won't be seen as a positive. Regardless, the failure to qualify from this group raises serious issues about Louis van Gaal.
Given more than £100 million to spend in the summer and following serious investment over the last few years - being unable to qualify ahead of a team fourth in the Bundesliga must raise the question of how much quality was bought in?
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The substitution of Nick Powell for Juan Mata highlighted a lack of both depth and quality in the squad. To make things worse, if you constructed a current world eleven, only David De Gea would currently compete for a place in the first eleven and even he would probably lose out to Manuel Neuer.
As one of the biggest football clubs in the world, the lack of quality is a concern but the problems are bigger than just that. While a 3-2 defeat might sound exciting and although Wolfsburg played very well, the defensive performance was worrying.
Until now, the one positive Man United fans had to shout about was the improvement of their defence this season. Even when they struggled to score, they were able to ground out narrow victories. But against the Germans they collapsed and were made to look very average.
Failure to qualify from this group puts Van Gaal's position at Old Trafford in doubt. Have they really progressed under his management?
Their league position would suggest they have, but watching them is rather like watching paint dry. Unrecognisable from the club's recent history, the tempo they now play at is equally worrying and depressing if you're a United fan.
All of this will lead to many calls for him to be sacked. This is very unlikely to actually happen but the pressure will now pass over to other competitions.