The Red Devils have failed to win a single Premier League title since such a campaign, with Michael Carrick the latest manager to try and end the unthinkable drought.
Countless managers have tried to emulate the Scotsman’s success at Old Trafford, but ultimately nobody has been able to emulate his sustained spree of silverware.
The hierarchy have spent some serious money trying to aid various managers in their quest for success, but it’s safe to say a lot of their investments have been a complete failure.
Why Antony is Man Utd's worst signing in recent years
After Erik ten Hag’s appointment as United manager, he was handed a war chest to improve the senior ranks - subsequently spending £86m to bring Antony with him from Ajax.
Such a fee for the second-highest paid for any player in the club’s history, with such a move undoubtedly generating huge excitement within the fanbase.
However, despite scoring on his debut against Arsenal, the 26-year-old failed to deliver at Old Trafford - finding the back of the net on just 12 occasions in his 96 outings.
The Brazilian often infuriated supporters with his spinning showboating, something which often saw him lose possession or fail to pick out a teammate.
Antony - Man Utd Record
Statistics
Tally
|
Cost
|
£86m
|
|
Games
|
96
|
|
Goals
|
12
|
|
Assists
|
5
|
|
PL Games
|
62
|
|
PL Goals
|
5
|
|
PL Assists
|
3
|
He subsequently joined Real Betis in January 2025, spending six months on loan in Spain, before permanently joining the LaLiga outfit in the summer window.
The winger would depart for a fee in the region of just £20m, which saw the Red Devils have to take a £66m loss on their investment just two years after his arrival.
His lack of impact, coupled with the loss made on his signature, has undoubtedly made him one of the club’s worst-ever additions and one that encapsulates the struggles since Sir Alex retired.
How one United star is becoming the worst signing since Antony
After such a disastrous move, you would think United would have learned from their failures, but the club continue to make numerous errors in the transfer market.
In the summer of 2024, the Red Devils paid a reported £60m for the signature of Uruguayan midfielder Manuel Ugarte in an attempt to overhaul the heart of the side.
However, prior to his recent injury, the hierarchy were looking to offload the 25-year-old, and the trio of new additions further highlights that he’s not part of Carrick’s plans.
The same transfer window saw Dan Ashworth sign striker Joshua Zirkzee from Italian side Bologna, with the club also paying £36.5m to bring the attacker to Old Trafford.
Many expected the Dutchman to be the man to solve the club’s issues within the final third, but a little over two years on, it’s clear that the deal for the 25-year-old has been a complete disaster.
He netted on his debut against Fulham in the 2024/25 campaign, which only fuelled the hope that he could be the next in a long line of elite-level forwards in Manchester.
However, he’s only netted four Premier League goals in his 56 outings since his debut strike, which has seen the likes of Benjamin Sesko leap ahead of him in the pecking order.
Despite huge rumours linking Zirkzee with a move away this summer, Carrick decided to keep hold of the attacker and hand him a fresh chance to star in the first team.
He’s been handed substitute appearances against Sabah, Manchester City and Brighton in recent weeks, but ultimately failed to deliver in all three encounters.
His stats in his 24-minute cameo on Wednesday night showcase his struggles and demonstrate why he’s rapidly becoming as bad of a signing as Antony.
Zirkzee could only register 17 touches of the ball after his introduction, but it was still enough to showcase his inability to deliver when having the ball at his feet.
The former Bayern Munich man failed to complete any dribbles or crosses into the 18-yard box, whilst putting his late header way wide of the target to try and salvage something at Old Trafford.
He could also complete just five passes during his late cameo, which ultimately saw him lose possession 10 times - a tally which was over half the amount of touches he registered.
His struggles were further compounded by losing 100% of the ground duels he entered, as the opposition were easily able to contain him after replacing Sesko.
His big-money transfer to United in the summer of 2024 has been nothing short of a disaster, with such a move deserving no more than a 2/10 at best.
If the club are to have any chance of returning to their former glory, it’s vital Zirkzee is moved on - even if they take a huge loss on his signature, as they did with Antony.
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