The Dutchman was evidently out of his depth long before Sir Jim Ratcliffe wielded the axe, and with Amorim having arrived off the back of a sensational season with Sporting, nothing but success was envisaged.
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Amorim wouldn't admit defeat at Man United over his formation
Unfortunately for the Portuguese and for the club's board, the rot soon set in.
To the point where press conferences were excruciating, and training sessions were a battlefield as Amorim sought to exert his authority over players who just couldn't understand his preferred system and formation, or execute his vision in the way in which he wanted.
Some might say that Amorim's single-mindedness in insisting that he wouldn't adopt any other tactical ideas and would simply keep working towards his stated aims was laudable.
After all, if a manager can't have carte blanche to shape a team as he sees fit, can he even be considered to be in charge at all?
Worst manager in Red Devils history
Ultimately, his way of working rarely produced the level of performance or results that were acceptable, and by the time he was removed from his position, he had earned the unenviable honour of having the worst win rate of any Man Utd manager in history: 36.2% overall, and 31.9% in the Premier League.
A damning indictment of his philosophy, that still didn't stop AC Milan hiring him to take over from Max Allegri, after the Rossoneri were beaten by Cagliari at San Siro on the final day of the 2025/26 Serie A season, to lose out on Champions League qualification.
Having officially taken over in early June, it's safe to say that Amorim hasn't had the best start to his career in Italy either.
On the eve of a pre-season friendly, ironically against a Man Utd side that are now going well under Michael Carrick, the Portuguese has overseen draws against Celtic and Inter, and a 3-0 loss against Chelsea.
History repeating already at Milan?
It's understood that, on the back of those three disappointing results, Amorim met with the board and doubled down on his intention to play five at the back, which served him well in the Portuguese league but not so much in the English top flight.
A case of history repeating perhaps?
Not unlike the way he discarded the likes of Alejandro Garnacho and Marcus Rashford at United, Amorim is already wielding the axe in Milan, and has told seven players that they're surplus to requirements and should find another club.
With all of Fikayo Tomori, Christopher Nkunku, Youssouf Fofana, David Odogu, Pervis Estupinan, Santiago Gimenez and Philip Terracciano being axed, Amorim is really putting his neck on the block.
This won't be another United MKII, though, as the Milan hierarchy are unlikely to let things slide for as long.
Amorim's reputation is on the line
The manager has staked his entire reputation on getting the best out of the players he has left, with one or two expected additions; if he still can't get things right, his future as a coach at the very top level is in doubt.
Although there is some sense in the exits - Gimenez only scored one Serie A goal in 2025/26, for example - it's still a huge risk from the manager, who has no room for error by making such a statement.
Not that he appears to be overawed by the task ahead of him.
"It's a very big challenge that I accepted, even if after the last one I told myself to accept a smaller one," he said to reporters recently.
"Perhaps it is a greater challenge than the last, but I'm at Milan to win, and if you're Milan coach you have to have this mentality.
"I'm not naive, I know there's a lot of work to do, but if you're the Milan coach you have to play to win."
With Rafael Leao's future still to be sorted out, too, there could yet be more upheaval at the club.
If Amorim can come up smelling of roses after all that, his tenure in Italy might finally put the nightmare in Manchester to the back of everyone's minds - and not before time as far as he's concerned.
Jason Pettigrove has been the features writer for Flashscore since 2025, utilising Opta data to form the basis of his articles. He has previously worked for high profile football clubs, news and media outlets, both in print and digital, and can usually be found watching FC Barcelona when time permits. You can read more of his pieces here.
