Ranking 7 Premier League clubs who ‘won the transfer window’ & flopped
Liverpool were widely acclaimed to have ‘won’ the 2025 summer transfer window – only to have endured a similar downfall to other Premier League clubs in the past.
With transfers almost an offshoot of the entire football industry by now, more is read into the activity of Premier League clubs than ever before.
But football remains, for now, a sport played on grass rather than paper and all the riches in the world didn’t prevent these big-spending sides from a sobering wake-up call.
7. Manchester United (2017-18)
United invested heavily in 2017, months after winning the League Cup and Europa League, only to fall short of expectations.
Romelu Lukaku scored plenty, but not enough to justify his £75million fee, while Nemanja Matic began his gentle decline on a fat United wage.
Expected to challenge for the title, Jose Mourinho’s team finished 18 points behind Manchester City and slumped out of the Champions League last 16 to Sevilla.
Mourinho would be sacked by the following Christmas, complaining about under-investment. Hah.
QUIZ: Can you name Jose Mourinho’s 25 most-used players at Man Utd?
6. Chelsea (2022-23)
The first year of the Todd Boehly era saw Chelsea spend over £500million to finish 12th under four different managers.
In the summer, Boehly prioritised experience with the likes of Raheem Sterling, Pierre-Emerick Aubameyang and Kalidou Koulibaly arriving in west London.
Disappointing results led to a total rethink, with Chelsea splashing big on young players in the winter window.
Mouths were agape when the Blues spent over £250million on Mykhailo Mudryk, Enzo Fernandez, Benoit Badiashile, Noni Madueke and Malo Gusto among others.
Mudryk is currently banned for taking performance-enhancing drugs, while Enzo Fernandez has rarely been a £100million player.
Neutrals revelled in Chelsea’s 2022-23 downfall, ending with Lampard back in interim charge and an outside chance of relegation.
Those days are sadly over now, with the Blues back in the Champions League and threatening to put a title charge together.
They are truly a club with an infuriating tendency to come out of sticky situations with zero consequences.
5. Everton (2019-20)
Back in their silly money era, Everton spent big on the likes of Moise Kean, Fabian Delph, Andre Gomes and Alex Iwobi in 2019 to widespread approval.
In time-honoured fashion, the Toffees sacked Marco Silva in December after falling into the relegation zone.
In less time-honoured fashion, Carlo Ancelotti was his replacement at Goodison Park. It still feels like a misprint on Ancelotti’s glittering CV.
But this was the last free-spending summer at Everton for years. Their waste meant finances were constrained and their horizons narrowed to just avoiding relegation.
Which they did, just, until moving to the Hill Dickinson Stadium in 2025.
4. West Ham (2024-25)
Having rid themselves of David Moyes, West Ham spent north of £150million on new signings to mark the start of the glorious Julen Lopetegui era
Niclas Fullkrug, Aaron Wan-Bissaka, Maximilian Kilman, Crysensio Summerville, Guido Rodriguez, Carlos Soler and Jean-Clair Todibo were all meant to be huge upgrades on the Hammers squad.
But Lopetegui was sacked by early January following several lame performances, leaving West Ham flirting with a relegation battle.
Graham Potter was somehow considered the answer, a delusion that lasted eight damaging months. West Ham are now deep in relegation trouble with limited finances and a woefully unbalanced squad.
READ: Ranking West Ham’s 23 mostly awful signings since winning the Conference League
3. Manchester United (2021-22)
Ole Gunnar Solskjaer added Raphael Varane and Jadon Sancho to his United squad that finished second in 2020-21 and everything seemed to be nicely falling into place.
Until Cristiano Ronaldo sensationally rejoined at the end of August.
Fans celebrated swiping Ronaldo from under Manchester City’s noses, but his arrival fatally unbalanced Solskjaer’s counter-attacking tactics.
Ronaldo scored 18 goals in the league, but United slumped to a miserable sixth in a campaign marked with several humbling defeats.
Solskjaer was sacked in November, following a 4-1 hammering at Watford, and interim replacement Ralf Rangnick declared ‘open-heart surgery’ was required on United’s squad.
Three years later, the operation has been a jaw-dropping failure and United are much further away from glory than ever before.
READ: 7 of the most infamous dressing room leaks in football history: Mourinho, Rangnick, Pulis…
2. Liverpool (2025-26)
Liverpool were comfortable Premier League champions in 2024-25, but chose to spend over £400million boosting their squad in the summer.
As it stands, only £69million striker Hugo Ekitike has been a success. Full-backs Milos Kerkez (£40million) and Jeremie Frimpong (£29million) have struggled, leaving the defence vulnerable.
But the headline misfires are Florian Wirtz (£100million) and Alexander Isak (£125million), who have only fitfully shown the form to justify their fee.
There’s a feeling that Arne Slot doesn’t know his best team or how to wean Liverpool off the Klopp-style system that brought them so much success.
The Reds have been awful this season, languishing in eighth after several humiliating results and Mohamed Salah in open mutiny.
There is every chance Liverpool will rectify the situation in the future, but it’s a proper bonfire at the time of writing.
1. Southampton (2022-23)
Forget Manchester City signing Erling Haaland; esteemed journalists were declaring Southampton as the winners of the 2022 summer window.
After winning one of their last 12 games of 2021-22, Ralph Hasenhuttl was backed with several young and promising signings as part of a squad overhaul.
But the Saints continued to struggle. Hasenhuttl was gone by November, Nathan Jones tanked their fortunes further, and Southampton finished rock bottom with 25 points.
They won instant promotion back to the Premier League, only to finish bottom again in 2025. With 12 points, this time.
Meanwhile, Haaland’s goals fired City to the treble. Sometimes the obvious answer is the right answer.
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