It’ll take a Herculean effort for a top-flight side to break into the higher echelons of the worst January transfer window signings ever made in the Premier League this season.
Over the years, some of the worst deals in England’s elite have occurred mid-season. Even the shrewdest of operators can come unstuck and often make rash decisions.
On paper, a lot of the transfers look like they will pay dividends. But of course, football is not played on paper and thousands of fans have been left bitterly disappointed with their club’s purchases.
Whether it seems like a financial steal or a team has paid over the odds, it’s quite rare that a January deal comes to fruition. Some switches have proved beneficial, though.
However, some transfers have been horrendous. And there are certainly some January deals that have been a lot worse than others.
Worst January Transfer Window Signings In Premier League History
17. Afonso Alves (Heerenveen to Middlesbrough £12.5m, 2008)
Afonso Alves made a fine impression when he joined Middlesbrough in the 2008 January transfer window. The Brazilian forward netted six times in his opening 11 Premier League games.
However, it went drastically downhill from there and he left Boro when the club were relegated in 2009. Alves will always be fondly remembered for his hat-trick against Man City in THAT 8-1 win.
16. Mykhailo Mudryk (Shakhtar Dontesk to Chelsea £62m, 2023)
As far as expensive January flops go, Mykhailo Mudryk is a solid addition. Chelsea thought they had got one over on Arsenal when they beat the Gunners to his signature in 2023.
Zero goals in his first 15 appearances proved otherwise. In total, he has netted 10 times in 73 outings for the Blues. The Ukranian is currently suspended after a failed drugs test in December 2024.
15. Cenk Tosun (Besiktas to Everton £27m, 2018)
Cenk Tosun strolled up to Goodison Park in 2018 with a relatively strong reputation for scoring goals at Besiktas. Ironically, Everton fans never got to see the Turk hit the back of the net too many times.
In fact, Tosun scored just nine times in over 50 appearances for the Toffees. The £27m signing actually re-signed for Besiktas in 2022.
14. Kim Kallstrom (Spartak Moscow to Arsenal on loan, 2014)
One of the worst January transfer window signings occurred in 2014 when Arsenal snared Swedish international Kim Kallstrom on loan. Despite the midfielder having a back injury!
Unsurprisingly, Kallstrom didn’t feature much as he underwent his rehabilitation in north London. He mustered just four appearances in all competitions and failed to make the matchday squad for the 2014 FA Cup final.
13. Gilberto (Hertha Berlin to Tottenham £2.5m, 2008)
Even the most hardened Premier League supporters will do well to remember Gilberto’s ill-plighted spell at Tottenham in 2008. Perhaps because he was shocking and got injured straight after joining!
The Brazilian left-back was out of his depth and featured just seven times in the Premier League. His error against PSV in the UEL led to defeat but he did score against West Ham in a 4-0 win. Was moved on in 2009. Ouch.
12. Wout Weghorst (Burnley to Man United on loan, 2023)
A glaring balls-up from Man United in the January window two years ago. The Red Devils signed Dutch international Wout Weghorst who promptly repaid the faith shown in him by scoring just twice in 31 outings.
To really put the cherry on top of the cake, Weghorst decided not to score a single Premier League goal for the Red Devils during his time at Old Trafford.
11. Jean-Alain Boumsong (Rangers to Newcastle £8m, 2005)
Jean-Alain Boumsong arrived at Newcastle with a fairly glowing reputation but there were oddities around the nature of the £8m transfer. Considering the Frenchman was available for free just a few months previous.
The defender started life at St James’ Park very well but then a catalogue of errors demonstrated his true colours. Was farmed off to Juventus when the Old Lady were relegated to Serie B.
10. Benni McCarthy (Blackburn to West Ham £2.25m, 2010)
When West Ham signed Benni McCarthy in 2010, they thought they were getting the Porto and Blackburn Rovers version of the South African legend. The Hammers were somewhat mistaken.
McCarthy failed to score a single goal in all competitions during his two-year stint in east London. The former forward had the last laugh after being given a £1.5m pay-off to leave the club.
9. Wilfried Bony (Swansea to Manchester City £25m, 2015)
No player scored more Premier League goals in the calendar year of 2014 than Wilfried Bony. That convinced Man City to part with £25m for the Swansea star.
However, the Ivorian’s move to the Etihad was a lot less fruitful in front of goal. He netted just ten times in 46 appearances before moving on to Stoke.
8. Jean Makoun (Lyon to Aston Villa £6.2m, 2011)
You have to go back 14 years for one of the worst January transfer window signings in Premier League history. Aston Villa were the guilty party when they forked out £6.2m for Jean Makoun.
The Cameroon international was sent-off in one of his first games for the club which resulted in a three-game ban. Makoun never really recovered and failed to make the grade at Villa Park.
7. Kostas Mitroglou (Olympiakos to Fulham £12.4m, 2014)
Kostas Mitroglou was Fulham’s club-record signing when he joined in January 2014. Brought in to help starve off the threat of relegation, Mitroglou was largely anonymous at Craven Cottage.
The Greek forward repaid the faith shown in him but scoring zero goals in his three top-flight appearances. Unsurprisingly, the Cottagers failed to stay up that season.
6. Guido Carrillo (Monaco to Southampton £19.1m, 2018)
A portion of the £75m Virgil van Dijk transfer fee was used on Guido Carrillo in 2018. The Argentine arrived at Southampton having helped Monaco to the Ligue 1 title the year previous.
Like some of the other entries on the list, Carrillo failed to score at St Mary’s in his seven appearances as the Saints just about avoided relegation.
5. Chris Samba (Anzhi Makhachkala to QPR £12.5m, 2013)
QPR’s disastrous dealings in the transfer market saw them part with a club-record £12.5 to sign Chris Samba from Anzhi Makhachkala in 2013.
The former Blackburn bruiser was paid £100,000-a-week to help keep the R’s up but made quite literally no difference to the cause. Amazingly, he was sold back to Anzhi in the summer for the same transfer fee.
4. Andy Carroll (Newcastle to Liverpool £35m, 2011)
2011 was a mental year which saw a strong contender for the worst January transfer window signing of all-time. Not just in the Premier League.
Andy Carroll moved from Newcastle to Liverpool and endured a truly miserable time at Anfield. The burly forward was actually a record signing and joined the same day as Luis Suarez. Wonder who went on to have the better career?
3. Fernando Torres (Liverpool to Chelsea £50m, 2011)
Staying with the theme of 2011’s madness, Fernando Torres made a mega-money move from Liverpool to Chelsea. His £50m price tag didn’t come close to being repaid.
However, the Spaniard did net THAT goal against Barcelona which Gary Neville still dreams about. In the Premier League, Torres scored just 20 times in three-and-a-half seasons.
2. Alexis Sanchez to Manchester United (swapped with Henrikh Mkhitaryan, 2018)
A rather strange deal that materialised in the winter of 2018. Arsenal ‘tricked’ Man United into taking what looked like a world beater in Alexis Sanchez off of their hands. In return, United snuck in ‘brilliant’ midfielder Henrikh Mkhitaryan.
Sanchez was afforded a £500,000-a-week deal and looked the shadow of his former self. He later admitted he made a mistake in going to Old Trafford where he never, ever looked at home.
1. Savio Nsereko (Brescia to West Ham £9m, 2009)
Here, you can look at every Premier League club’s January signings from 2025 but it’s borderline impossible one will be as bad as Savio Nsereko’s move to West Ham in 2009.
Nsereko has scored just 25 times in a career that has seen him play in Bulgaria, Romania and Kazakhstan. He was actually purchased to replace a prime Craig Bellamy but was simply awful. Dreadful in fact.
