Marcus Rashford was then sent off, allowing the hosts to draw level before the break. A Bruno Fernandes penalty nudged Ten Hag’s side ahead once more, only for two late Copenhagen goals to condemn them to defeat.

It leaves the Red Devils bottom of their Champions League group ahead of their final two fixtures against Galatasaray and Bayern Munich. The defeat also saw Man United secure their own slice of unwanted history.

According to Opta, it was the first time that the club had fallen to defeat in the Champions League having gone two goals ahead. It was also the first time that had happened in all competitions for nearly a decade.

The last time it happened in the Premier League came back in September 2014 with a 5-3 defeat to Leicester under the tutelage of another Dutch coach – Louis van Gaal. The Red Devils had gone 2-0 up against the newly-promoted Foxes via a Robin van Persie header and a stunning chip from Angel Di Maria at the King Power Stadium.

Jamie Vardy celebrates scoring against Man United in a 5-3 win for his side ( Image: Getty Images)

Leonardo Ulloa gave Leicester hope, only for Ander Herrera to seemingly put the game beyond the hosts. However, the East Midlanders managed to revive themselves as David Nugent, Esteban Cambiasso and Jamie Vardy all found the net in the second half before Ulloa wrapped up three points late on – Tyler Blackett also being sent off on a nightmare afternoon.

Despite another rotten evening, Ten Hag was full of praise for the way his side performed against Copenhagen and claimed Rashford’s dismissal was the turning point. Speaking in his post-match press conference, he said: “We are very disappointed because we played very good.

“We started the game so well. Our best minutes of the season. We are winning the game and the red card changes everything.”

The Red Devils are back in action this weekend in the Premier League. They have a great chance to make it back-to-back league victories as they take on struggling Luton at Kenilworth Road.

The Hatters have only won one out of their 11 games so far this term following a surprise promotion but held Liverpool to a 1-1 draw last time out. United sit eighth in the Premier League ahead of this weekend’s game but could jump to sixth with a win.