Manchester United are in the midst of a challenging 2026 transfer window. Hopefully it won’t be as bad as any of these…
It is accurate to say that Manchester United’s transfer history has been full of missed opportunities over the years. And often the choices United have made turned out to be poor ones.
Here is a look at the six worst transfer windows ever…
2009: The all-time letdown
- IN: Antonio Valencia, Gabriel Obertan, Michael Owen
If you want to try and pinpoint the moment Manchester United’s decline started, it was actually the summer of 2009.
United sold Cristiano Ronaldo for a club record fee at £80 million, and also made the decision not to re-sign Carlos Tevez. This left only Wayne Rooney and Dimitar Berbatov in attack, and fans expected big signings.
Instead, we landed Michael Owen on a free transfer. While he was keen to prove a point, Owen was well past his best, and too injury-prone to make an impact. He should never have been the focal point of United’s summer business.
United had shown interest in Lyon’s Karim Benzema, but Real Madrid pushed harder and signed him alongside Ronaldo. That was real ambition.
What happened to the United that spent so ambitiously in 2007 and saw the team deliver the Champions League a year later?
In 2009, United were coming off a Champions League Final defeat and fans expected a statement. But the further additions beyond Owen were Antonio Valencia, a solid but uninspiring signing, and Gabriel Obertan, a disastrously poor addition.
This was an all-time letdown of a window that left Wayne Rooney publicly questioning the club’s ambition. Sir Alex Ferguson was able to hold the team together, but as soon as he left, it all began to fall apart.
2013: A disastrous new era
- IN: Marouane Fellaini
This one still haunts us now. How could Manchester United, the reigning champions in 2013, deliver only one player to the long-awaited successor for Sir Alex Ferguson?
Looking back, it is clear that David Moyes never stood a chance of success. He certainly contributed to his own downfall with some of his decisions, words, and tactics, but the club’s transfer business was pure incompetence.
Ferguson handpicked Moyes as his successor, and anybody stepping into that role deserved to be backed properly.
The problem was David Gill‘s retirement along with Ferguson, and the Glazers elected to appoint Ed Woodward as his successor. It was a name few Manchester United fans knew – but certainly did by the end of the window.
There was no strategy, other than failed pursuits of Cesc Fabregas and Gareth Bale. Woodward was chasing a big name statement signing, and missed.
Moyes spurned a possible move for Thiago Alcantara, although there is no guarantee Woodward might have been able to get it done.
Everything United touched turned to disaster. Fake Spanish lawyers impeded an attempt to activate Ander Herrera’s release clause.
United then settled on a deal for Marouane Fellaini, paying an extra £4 million after missing an earlier deadline. Moyes wanted Leighton Baines too – and could not even get that done.
It was no surprise that Moyes failed to even complete one of the six years he was contracted to.
2018: The end of Mourinho
- IN: Diogo Dalot, Fred, Lee Grant
Jose Mourinho infamously declared that leading Manchester United to second place in 2017/18 was his greatest achievement. It was at least a sign of upward progress.
Mourinho wanted to be backed in the market to mount a serious title challenge. What he got simply was not good enough.
Ed Woodward delivered a teenage right-back, an unproven midfielder from the Ukrainian league, and a back-up goalkeeper.
All three deals were struck by early July, and then United simply shut up shop and did not spend another penny.
It was no wonder that Mourinho became increasingly tetchy as the summer went on, making his irritation clear during the club’s pre-season tour.
Mourinho ended up paying for United’s poor transfer business with his job. He was fired four months into the new season.
He was keen to land two players in-particular, Ivan Perisic and Harry Maguire. Ed Woodward refused to pay up – before spending an even higher fee to land the latter 12 months later.
2020: Another post-Champions League miss
- IN: Donny van de Beek, Alex Telles, Facundo Pellistri, Edinson Cavani, Willy Kambwala, Amad
The transfer window in 2020 followed the trend of 2018, that Manchester United rested on their laurels after qualifying for the Champions League.
After rebuilding under Ole Gunnar Solskjaer and finishing third in the Covid season, United fans expected big investment. But the 2020 window did not go to plan.
United spent weeks chasing Jadon Sancho, before eventually giving up. The club then blew £35 million on Donny van de Beek.
Van de Beek had all the credentials, but it soon became clear that Ole Gunnar Solskjaer had no plans to actually play him. It was a wasted investment.
This was the entirety of the transfer window before a disastrous 6-1 defeat at home to Mourinho’s Tottenham.
The embarrassing home loss led to a spree of transfers on deadline day. Edinson Cavani was, to be fair, a shrewd short-term addition.
Amad proved a smart long-term move, although he did not finalise his transfer until the following January.
As a whole, this was not the transfer window that United needed. Top clubs should not be panicking around trying to do the majority of their business on deadline day. The late flurry served to highlight the dysfunction at the club.
2021: Ronaldo accelerates decline
- IN: Jadon Sancho, Tom Heaton, Raphael Varane, Cristiano Ronaldo
In theory this was a dream transfer window for Manchester United fans. The club scooped up long-linked target Jadon Sancho for a discounted price compared to previous touted fees. But it was still too much.
Raphael Varane was a classy addition in defence, although one who lasted only three seasons.
And then there was the blockbuster panic move for Cristiano Ronaldo.
Ronaldo’s return was a dream for United fans, but there was absolutely no strategy behind it, other than to stop City signing him.
The Ronaldo signing ended up accelerating Solskjaer’s exit as manager, or causing it entirely, depending on your point of view.
On the face of it, a Sancho, Varane, Ronaldo transfer window sounds great. Many fans thought at the time that we had struck gold – but none of the signings were really what United needed, and it backfired.
The season had started so positively with a 5-1 thrashing of Leeds at Old Trafford. Within three months, Solskjaer was sacked, and United had written the season off by appointing Ralf Rangnick as interim manager.
Jadon Sancho was clearly not the player he was cracked up to be, and Solskjaer later admitted confusion over his best position.
United would have been far better served by spending the Sancho fee on a midfielder like Declan Rice, while if after a winger – Michael Olise was available at a fraction of the price.
2023: Ten Hag’s worst choices
- IN: Mason Mount, Andre Onana, Rasmus Hojlund
Manchester United spent a combined £166 million to sign Mason Mount, Andre Onana and Rasmus Hojlund, and all three players flopped.
This window was crucial for Erik ten Hag’s side to start progressing after a promising opening season in charge.
The decision to move on from David de Gea was overdue yet handled poorly. It was made worse by the choice of replacement, with Andre Onana unconvincing from the very start.
Mason Mount was an odd fit tactically, and that’s before even getting into the injury issues that have blighted his career.
Rasmus Hojlund needed an experienced striker with him to help him out. He was asked to do too much and struggled with the pressure.
For the amount of money United spent in this window, the club could have signed Harry Kane and delivered a genuinely world class striker.
Ten Hag was sacked a year after this transfer window, and will no doubt have regrets about how it all played out.
Which was the WORST Man Utd transfer window of all time?
There have been many bad transfer windows for United – but which was the most costly?
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