Harry Kane assisted Kingsley Coman’s goal that sent the Red Devils crashing to a 1-0 defeat and sealed their fate at the bottom of the group also containing Copenhagen and Galatasaray.
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History was made with that result too, with Man Utd conceding more goals than any other English team in Champions League group stage history.
A number of top stars also went missing, including £72million man Rasmus Hojlund, though he cannot be blamed for a lack of service or competence to help create threats behind him.
It was the third time in seven seasons that they have been in the Champions League since Sir Alex Ferguson retired that the club has been knocked out at the group stage.
However, there was one occasion when Man Utd had just as bad a time this year as they did under the legendary manager.
Back in the 2005/06 season, Man Utd finished bottom of a group with Villarreal, Benfica and Lille with a 2-1 defeat to Benfica on the final day at Lisbon’s Stadium of Light sending them out of Europe completely.
But who was starring for Man Utd then? And is there a modicum of optimism for the future considering the 2005 team went on to win the Champions League in 2008?
Edwin van der Sar
Edwin van der Sar started in goal in this game but was unable to prevent Geovanni and Beto from scoring for Benfica.
Would be the penalty shootout hero in 2008 when Man Utd beat Chelsea on penalties in Moscow, Russia, with the Dutchman saving Nicolas Anelka‘s spot kick to win the game.
Gary Neville
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A Man Utd veteran but still at the top of his game by this point, BBC‘s match report said Gary Neville delivered the “perfect cross” into the box for Man Utd’s goal after six minutes.
Club captain Neville was absent from the 2008 final due to injury.
Rio Ferdinand
Rio Ferdinand starred in central defence in this game, and it was just one month later that Man Utd would go and bring in Nemanja Vidic.
That partnership would go on to lift five Premier League titles and start the 2008 Champions League final, but Ferdinand was powerless to prevent Man Utd’s fall in 2005.
Mikael Silvestre
Always reliable during his time at Man Utd, Mikael Silvestre had joined the season after the 1999 treble-winning campaign before he would go on to leave just after the 2008 win.
He would be on the bench in the 2008 final and like Ferdinand had been powerless to prevent the embarrassment of finishing bottom of the group.
John O’Shea
Another name who would be on the bench when Man Utd lifted the trophy in 2008, John O’Shea starred at left-back against Benfica.
Like Silvestre, Man Utd made a key addition to the position by bringing in Patrice Evra the month after this game.
Cristiano Ronaldo
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Said to have had a horrid time on his return his Lisbon, Cristiano Ronaldo was still a raw and inconsistent bundle of talent, even showing off his petulant side when he was booked for kicking Beto.
However, given time to mature he soon became one of the best players in the world and scored in the 2008 final.
Alan Smith
It was Alan Smith’s poor defensive header in the Benfica game which allowed Beto to score the winner just before half-time.
Smith would be sold to Newcastle in 2007 and continued to be a Premier League regular until 2011.
Paul Scholes
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Paul Scholes scored the opener for Man Utd after six minutes and was at the core of everything positive the team did on the night.
Continued to star for the club until his full retirement in 2013 – notwithstanding the gap year he had in 2012 – and played 87 minutes of the 2008 final.
Ryan Giggs
Combined with Neville for Scholes’ opener but Ryan Giggs could not work anymore of his magic and was hooked after 60 minutes for Louis Saha.
Came on off the bench in the 2008 final with his role becoming more reserved as the years went on.
Wayne Rooney
Like Ronaldo, Wayne Rooney was still a raw talent yet to really come into his own and was part of a largely non-existent attack throughout most of the game.
Would go on to start the Champions League final two seasons later after maturing into one of the world’s best forwards.
Ruud van Nistelrooy
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This game proved to be Ruud van Nistelrooy‘s final Champions League game in a Man Utd shirt, though he linked up well with team-mates throughout the tie.
He finished as the squad’s top scorer for the season with 24 goals but he was sold to Real Madrid the following summer.
Future hope?
With Sir Jim Ratcliffe hoping to complete his 25 per cent buy-in soon, the optimists among the Red Devils fanbase may hope for similar additions to what was seen in 2005 next month.
Of course, then Man Utd had Ferguson and David Gill running the show.
But since their departure, a lack of clear strategy has seen the club flounder into mediocrity and there is unlikely to be any kind of quick fix for it.
Though a long-term plan can begin to be implemented once the pieces fall into place.
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