The winter window is a tempting time to do business, potentially giving a club an edge in the race for silverware, survival or the chase for Europe.
2025's January transfer window is now open, with business on the quiet side compared to previous years. Arsenal are looking for a forward, City may splash the cash and Ruben Amorim may make his first senior signing as Manchester United manager.
There’s a reason why Premier League managers try to avoid doing too much business at the turn of the year, though. More mistakes tend to be made in January, with FourFourTwo looking at some of the biggest mistakes in date order.
1. Mykhailo Mudryk (Shakhtar Donetsk to Chelsea £89 million, 2023)
Eyebrows were raised when Chelsea splashed over £85 million on a winger who had scored just nine goals in his career. The hefty price tag has not helped the pressure on Mudryk's shoulders with the Ukrainian scrutinised from his first touch.
However, his time at Chelsea has been woeful, scoring just five goals in 53 matches and failing to live up to the hefty price tag. Under Enzo Maresca Chelsea are thriving but Mudryk has still not become a key part of the new manager's plans, instead the £89 million pound man is saved for the European Conference League.
2. Henrikh Mkhitaryan and Alexis Sanchez (Swap deal, 2018)
Widely regarded as one of the worst swap deals of the 21st century, Henrikh Mkhitaryan moved to Arsenal from Manchester United, with Alexis Sanchez moving in the other way. Sanchez, who ranked at No.15 in FourFourTwo's list of the best Premier League wingers of all time, had been a revelation at Arsenal. But he wanted to improve his chances of winning trophies, despite winning two FA Cups at Arsenal, and pushed through a move to Manchester United.
Trophies did not materialise with the Chilean scoring just three goals in 32 appearances. Mkhitaryan fared slightly better, lasting just over half a season and scoring eight times. But the hype around the swap was far far bigger than the performances the players delivered.
3. Cenk Tosun (Besiktas to Everton £27 million, 2018)
Having bagged over 40 goals for Besiktas in two seasons, Tosun seemed like a shrewd signing for Everton. However, the Turkish international failed to acclimatise to England. A revolving door of managers at Goodison Park, and an upturn in the form of Dominic Calvert-Lewin did not help either.
He returned to Besiktas four years later, via a loan at Crystal Palace, having played 55 times in England and bagging just 10 goals at a cost of nearly £3 million a goal for Everton.
4. Guido Carrillo (Monaco to Southampton £19.1m, 2018)
Having £75m burning a hole in your pocket can do strange things to a football club. After selling Virgil Van Dijk to Liverpool, relegation-threatened Southampton fancied a statement signing to show fans they were still ambitious – that, and securing more firepower having averaged only a goal a game under Mauricio Pellegrino by the end of January.
It turned out that Carrillo wasn't the answer. A big-money acquisition who'd helped Monaco to the Ligue 1 title in 2016/17, the Argentine striker ultimately started just seven games (five in the league) and never scored for the Saints as they narrowly survived. Incoming manager Mark Hughes played him just twice from mid-March, and he was farmed out on loan to Leganes in 2018 before leaving permanently in 2020.
5. Juan Cuadrado (Fiorentina to Chelsea £23.3m, 2015)
League leaders from the off, Chelsea didn't need to do much in January 2015; indeed, it was mostly Jose Mourinho confirming the exits of fringe players like Andre Schurrle, Mark Schwarzer, Fernando Torres and Ryan Bertrand, the latter two formalising existing loan deals. The only incoming signature was sealed on 2 February 2015: fleet-footed Fiorentina flanker Juan Cuadrado.
Having given the Colombian just four starts, Mourinho, who ranked at no.12 in FourFourTwo's list of the greatest managers ever, said "He'll be amazing next season" – and indeed he did impress, but on loan at Juventus, who signed him permanently in summer 2017. The kicker? As part of the £22.3m deal that had taken Cuadrado to Chelsea, the Blues had loaned Fiorentina a winger called Mohammed Salah...
6. Kostas Mitroglou (Olympiacos to Fulham £12.4m, 2014)
There’s putting all of your eggs in one basket, and then there’s Fulham signing Mitroglou for a club-record fee in early 2014. Granted, the Cottagers did also bring in Johnny Heitinga and Lewis Holtby on deadline day, but Olympiakos’s prolific marksman was identified as the player who could score the goals to keep Rene Meulensteen’s men in the Premier League.
Except he couldn’t. Unfancied by Meulensteen’s successor Felix Magath, Mitroglou started just one game in English football as the Cottagers tumbled into the Championship.
7. Kim Kallstrom (Spartak Moscow to Arsenal loan, 2014)
This was a truly bizarre acquisition, even if it didn’t cost Arsenal a transfer fee. The Gunners desperately needed a striker in the mid-season window in 2013/14 (and, as ever, a centre-back and defensive midfielder wouldn't go amiss) – but instead Arsene Wenger opted to bring in an ageing, injury-prone attacking midfielder on a four-month loan deal.
Unsurprisingly, Kallstrom’s debut was delayed due to fitness problems, Arsenal having gone ahead with the deal despite discovering back issues in the Swede’s medical. He finally made his bow against Swansea in late March, one of only four appearances for the north Londoners before returning to Spartak Moscow at the end of the campaign.
8. Fernando Torres (Chelsea to Liverpool £50m, 2011) and Andy Carroll (Newcastle to Liverpool £35m, 2011)
There were already signs that Torres was on the wane when he swapped Anfield for Stamford Bridge in January 2011, but Chelsea learned the hard way; a hefty fee of £50m bought just 20 Premier League goals across three-and-half seasons, and gave Liverpool fans the chance to gloat.
Or at least it would have done had the Reds not splurged most of the proceeds on Andy Carroll, who is Liverpool's tenth-most expensive signing ever. He managed 11 goals in 58 appearances and was entirely unsuited to the Reds’ style of play throughout his miserable 18 months on Merseyside.
9. Savio Nsereko (Brescia to West Ham £9m, 2009)
As of January 2025 some of Savio’s last clubs have been Atyrau (Kazakhstan), Lietava Jonava (Lithuania), Beroe Stara Zagora (Bulgaria) , Pipinsried (Germany) and BSC Sendling (Germany) which probably says more about his true level of ability than his £9m move to West Ham at the start of 2009.
The Hammers handed the former Germany U20 international their No.10 shirt at Upton Park, but he failed to live up to expectations and made just a single Premier League start (he appeared in nine other games from the bench) before being shipped off to Fiorentina seven months later.
10. Afonso Alves (Heerenveen to Middlesbrough £12.5m, 2008)
Signing strikers from the Dutch top flight is a hit-and-miss business. For every Ruud van Nistelrooy there is a Vincent Janssen, for every Luis Suarez a Mateja Kezman, and for every Robin van Persie a Siem de Jong.
Afonso Alves, unveiled by Middlesbrough in truly bizarre fashion, was another member of the "miss" masses. Having bagged 45 goals in 39 Eredivisie games for Heerenveen, he scored just 10 in 42 during 18 months in a Boro side that eventually succumbed to relegation.
11. Jean-Alain Boumsong (Rangers to Newcastle £8m, 2005)
This was an odd acquisition on many levels, with Graeme Souness's Newcastle paying Rangers £8m for Boumsong’s services just a few months after he’d been available on a free. Indeed the transfer was closely examined by the 2007 Stevens inquiry, although it found no irregularities.
The 27-time France international actually started his career at St James’ Park well, but basic defensive errors soon began to creep into his game. Juventus, having been relegated to Serie B just a few months previously, took Boumsong off the Magpies’ hands in August 2006, though he never featured in Serie A once the Old Lady made it back.
