The Premier League's Transfer Disasters: 25 Windows of Regrettable Signings

English football's transfer market has served up some genuinely dreadful deals over the past quarter-century. We've compiled the worst signing from each of the last 25 windows—a rogues' gallery of inflated fees, misguided recruitment, and players who simply never delivered.

Winter 2014 – Kostas Mitroglou (Olympiacos to Fulham, £13m)

The Cottagers' record signing at the time arrived in January 2014 with an impressive pedigree: 14 goals in 12 Greek top-flight matches and three in five Champions League appearances. Yet those credentials evaporated entirely at Craven Cottage. Three appearances, mostly hampered by injury, and a swift loan return to Greece told the story. Former Fulham midfielder Steve Sidwell offered a memorable assessment of the striker's time in London, recalling his constant consumption of protein bars around the training ground.

Summer 2014 – Angel Di Maria (Real Madrid to Manchester United, £67m)

Fresh from winning the Champions League final's player-of-the-match award, the Argentine superstar looked destined for greatness at Old Trafford. Instead, he managed just four goals and looked thoroughly disengaged throughout his stint. Gary Neville later reflected that Di Maria "was never interested from day one." The club cut their losses when PSG came calling in 2015, limiting the damage to around £14m.

Winter 2015 – Wilfried Bony (Swansea to Manchester City, £28m)

Bony's move from Wales to the title-chasing Cityzens seemed logical on paper. The Ivorian had been a lynchpin of Swansea's attack, but he couldn't replicate that form at the Etihad. Eleven goals in 46 appearances told the tale of disappointment. Mercifully, Swansea took him back for approximately £11m two-and-a-half years later.

Summer 2015 – Memphis Depay (PSV to Manchester United, £30m)

United's £30m outlay on the Dutch winger proved poorly timed or simply ill-suited to English football. Despite seven goals across his Old Trafford tenure, Depay flopped spectacularly. He'd arrived with genuine excitement following his PSV exploits, only to eventually find his form in France with Lyon.

Winter 2016 – Oumar Niasse (Lokomotiv Moscow to Everton, £16m)

The Everton acquisition's nine goals in 42 appearances might sound respectable on the surface, though anyone who witnessed his performances knew better. Now 35 and retired after a stint at Macclesfield, Niasse's move represented a hefty investment that simply didn't justify itself. Giannelli Imbula's £22m flop at Stoke in the same window deserves honourable mention.

Summer 2016 – Shkodran Mustafi (Valencia to Arsenal, £35m)

Arsenal's £35m gamble on the World Cup-winning defender backfired spectacularly. Error-prone and unreliable, Mustafi became a liability under both Wenger and Emery. Remarkably, he managed to avoid defeat for 20 consecutive matches before finally losing—suggesting he'd been trying his hardest to tank results from day one.

Winter 2017 – Saido Berahino (West Brom to Stoke, £13m)

The prospect who'd netted ten times in eleven England Under-21 matches looked destined for bigger things. His move to Stoke proved otherwise. Five goals across two-and-a-half seasons preceded a journey through Belgium, Cyprus, India, and Slovenia. The 32-year-old now finds himself without a club.

Summer 2017 – Danny Drinkwater (Leicester to Chelsea, £34m)

The midfield recruit from Leicester's title-winning squad couldn't replicate that success at Stamford Bridge despite Chelsea's £34m investment. Drinkwater himself later described the move as a "shambles"—a fair assessment of a transfer that also saw Alvaro Morata and Tiemoue Bakayoko arrive at the Bridge.

Winter 2018 – Alexis Sanchez (Arsenal to Manchester United, swap deal)

The Chilean's best moment in a United shirt came during his piano-playing video announcement. His on-pitch contributions proved far less melodious. The swap that brought Henrikh Mkhitaryan to Arsenal worked out poorly for both parties, though Mkhitaryan's struggles in London provided little consolation.

Summer 2018 – Kepa (Athletic Bilbao to Chelsea, £72m)

Chelsea's decision to shatter the goalkeeper transfer record by spending over £70m on Kepa looked catastrophic almost immediately. Frank Lampard's subsequent recruitment of Edouard Mendy exposed the Spaniard's shortcomings so thoroughly that the upgrade felt instant and undeniable.

Winter 2019 – Denis Suarez (Barcelona to Arsenal, loan)

Arsenal's loan strategy proved baffling once again. Having paid £600k to loan Kim Kallstrom in 2013/14—the midfielder managed just 135 minutes—the Gunners repeated the experiment by investing over £2m to bring in Suarez from Barcelona. The Frenchman played meaningful minutes in exactly one of his six appearances, accumulating barely 20 minutes of action across the rest.

Summer 2019 – Tanguy Ndombele (Lyon to Tottenham, £52m)

Tottenham's record-breaking £52m recruitment of the French midfielder initially looked promising, but Ndombele swiftly became a burden. His subsequent journey—loaned to Lyon, shipped to Napoli, then Galatasaray before joining Nice on a free transfer in 2024—illustrated the scale of the miscalculation.

Winter 2020 – Ally Samatta (Genk to Aston Villa, £10m)

While hardly a catastrophic investment, Samatta's half-season at Villa Park yielded little. Two goals, including a header in the Carabao Cup final defeat to Manchester City, didn't justify the outlay. He found more success on loan at Fenerbahce, eventually signing permanently with the Turkish club.

Summer 2020 – Rhian Brewster (Liverpool to Sheffield United, £23m)

The striker's £23m move from Anfield to Bramall Lane proved underwhelming. Nine goals across 119 matches represented poor return on investment. Brewster, now 26, has since moved to Derby County.

Winter 2021 – Morgan Sanson (Marseille to Aston Villa, £13.9m)

Few remember this £13.9m signing at all—perhaps the most damning indictment possible.

Summer 2021 – Romelu Lukaku (Inter to Chelsea, £97.5m)

Chelsea's near-£100m gamble on the Belgian striker has aged terribly. Lukaku scored sporadically, made his desire to leave abundantly clear, then delivered embarrassing performances before returning to Inter on loan. The transfer epitomised the club's increasingly chaotic recruitment strategy.

Winter 2022 – Philippe Coutinho (Barcelona to Aston Villa, £17.6m)

Expectations ran high when the Brazilian arrived, but Coutinho's Villa Park tenure proved a massive letdown. Six goals and three assists across 43 appearances represented a significant underperformance for a player who cost just short of £20m.

Summer 2022 – Antony (Ajax to Manchester United, £85.5m)

Manchester United's £85.5m expenditure on the Brazilian winger proved catastrophic, particularly given Erik ten Hag could have secured him for half the price earlier in the window. Antony's subsequent revival at Real Betis only sharpened the sting of the original decision.

Winter 2023 – Mykhaylo Mudryk (Shakhtar to Chelsea, £62m)

The Ukrainian's performance-enhancing drugs suspension cast a shadow over an already underwhelming Chelsea signing. His performances beforehand offered little evidence of PED-enhanced abilities, making this arguably the most straightforward inclusion on the list.

Summer 2023 – Andre Onana (Inter to Manchester United, £47m)

Ten Hag's favoured goalkeeper proved catastrophic in practice. Onana's individual errors directly contributed to United's Champions League elimination, with his mistake-riddled displays eventually forcing his replacement by Senne Lammens the following summer.

Winter 2024 – Kalvin Phillips (Manchester City to West Ham, loan)

The loan move promised regular football and England selection ahead of Euro 2024. Instead, it became a disaster for all involved. Phillips' debut saw him commit an error leading to a goal within three minutes, and his performances never recovered. Bizarrely, once he actually started playing regularly, he stopped receiving England caps.

Summer 2024 – Odysseas Vlachodimos (Nottingham Forest to Newcastle, £20m)

The Greek goalkeeper's £20m transfer to Newcastle represented pure accounting gymnastics—a PSR-compliant move that served no footballing purpose. Playing just 45 competitive minutes, Vlachodimos existed primarily to balance Newcastle's books in facilitating Elliot Anderson's £35m move to the City Ground. The valuation disparity—effectively pricing Anderson at £15m—illustrated the absurdity of the deal.

Winter 2025 – Mathis Amougou (Saint-Etienne to Chelsea, £12m)

Chelsea's continued recruitment chaos produced this £12m signing from Saint-Etienne. Amougou managed 22 minutes before being offloaded to sister club Strasbourg less than five months later—a perfect encapsulation of the club's chaotic Todd Boehly era.

Summer 2025 – Yoane Wissa (Brentford to Newcastle, £55m)

Newcastle's £55m gamble on the 29-year-old winger already looks regrettable. While alternatives like Anthony Elanga offer youth as mitigation, Wissa's move carried obvious risk from the outset and has failed to deliver. The Magpies clearly harbour serious doubts about the decision.

Winter 2026 – Pablo (Gil Vicente to West Ham, £20m)

A relatively quiet transfer window left slim pickings, but West Ham's £20m Portuguese signing stands out for all the wrong reasons. Zero goals across nine appearances represents a genuinely disappointing start to his Premier League career.