The January transfer window is a risky time to enter the market in search of new talent. 

With squads settled and rhythms formed, it's particularly challenging for a new player to make an impact after arriving midway through the season. 

That acknowledgement, however, does not deter clubs from using the window as an opportunity to bolster their squad and give themselves the best possible chance of achieving their objectives for the season. 

There are countless examples of misguided January deals gone wrong, from mega-money strikers to bizarre loan deals. 

With that in mind, and with clubs across Europe now allowed to venture into the market in search of fresh blood, GIVEMESPORT have rounded up 20 of the worst January signings in the history of the Premier League. 

Take a look at our ranking in descending order as we count down to the worst winter window acquisition in the division's history...

20. Denis Suarez to Arsenal

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Unai Emery brought Spanish playmaker Denis Suarez to the club on transfer deadline day in 2019, but the former Manchester City youth prospect made just six substitute appearances in a forgettable spell.

19. Hossam Ghaly to Tottenham Hotspur

Hossam Ghaly will be remembered as the man who controversially threw his Spurs shirt down in front of Martin Jol in disgust after suffering the indignity of being substituted having initially come off the bench.

It's one of the most embarrassing things that can happen to a professional footballer, and Ghaly never recovered from that moment before eventually leaving the north London outfit in 2009.

18. Kim Kallstrom to Arsenal 

Another of Arsenal's bizarre loan deals took place in 2014. 

The Swedish midfielder, who made 131 appearances for his country in a fantastic career, played just 128 minutes of Premier League football in a six-month spell.

17. Cenk Tosun to Everton

One of Sam Allardyce's big-money Everton signings has failed to make an impact in the Premier League. 

The Turkey international has scored just ten times in 56 games since joining the Toffees in 2018 for a reported £27m fee.

16. Jean-Alain Boumsong to Newcastle United

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Newcastle spent £8m on Jean-Alain Boumsong just months after he signed Rangers on a free, and his performance never warranted what was a sizable fee in 2005. 

15. Oumar Niasse to Everton

Oumar Niasse was never good enough for Everton, and if anything his return of nine goals in 42 games actually lends some reason to believe that his place on this list is rather harsh. 

However, it was Niasse's all-round game that left so much to be desired and one would have to physically watch him in action to understand what the stats cannot reveal. 

At £16.1m the Senegal international was a poor piece of business.

14. Fernando Torres to Chelsea

Chelsea sanctioned a £50m move for Fernando Torres before it was customary to splash sums of that magnitude in the market. 

Though Torres' return of 45 goals and 35 assists in 172 outings is far from a disastrous return, the Spaniard struggled to replicate the level of scintillating flair he showcased so regularly at Liverpool. 

The Blues expected much more at that price.

13. Andy Carroll to Liverpool

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Back when Andy Carroll's career was in the ascendancy, the towering striker was rewarded for his excellent form at Newcastle with a £35m move to Liverpool in January 2011. 

He bagged an emphatic brace on his third Premier League start for the Reds, but it proved to be a false dawn.

Carroll managed just 11 goals in 58 games for the club and Liverpool ultimately made a £20m loss when they sold him to West Ham two-and-a-half years later.

12. Saido Berahino to Stoke City

Saido Berahino's career only went in one direction following his failed attempt to engineer a move from West Brom to Spurs in 2015.

The striker eventually got his wish to depart and moved to Stoke City for an initial £12m in January 2017, though he scored just five goals in 56 games for the club.

11. Wahbi Khazri to Sunderland

A versatile attacking player who failed to discover anything close to a potent run of form in English football, Wahbi Khazri netted three times in 42 Sunderland appearances.

10. Chris Samba to Queens Park Rangers

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The infamously well-paid Chris Samba couldn't prevent QPR from being relegated to the Championship following his arrival in January 2013.

Samba managed to get himself embroiled in a Twitter spat with QPR supporters, who he suggested should just get over his reported £100k-per-week salary, before returning to Anzhi Makhachkala the following summer.

9. Jordan Hugill to West Ham

Sensing a theme by now? January's a bad time to buy a new striker.

Jordan Hugill's modest form for Preston in the Championship earned him a £10m switch to West Ham in January 2018.

He played just 22 minutes of football for the Hammers before joining Norwich in August 2020.

8. Jurgen Locadia to Brighton & Hove Albion

Brighton signed Jurgen Locadia for a then club-record £14.1m fee in 2018 in light of the centre-forward's prolific return at PSV Eindhoven.

Locadia could not replicate his form in Holland on English soil, however, as he notched just three goals in 34 Premier League outings before moving on loan to Hoffenheim and now Cincinnati.

7. Gianelli Imbula to Stoke City

Gianelli Imbula was a Football Manager and FIFA Career Mode dream but his digital quality did not translate in reality.

The combative midfielder became the club's record signing at £18.3m move from Porto, but his contract was eventually cancelled by mutual consent four years and 28 appearances later.

Imbula is currently a free agent at 28 years old.

6. Wilfried Bony to Manchester City

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Manchester City's move for Wilfried Bony made perfect sense given his prolific record at Swansea City, but the £25m man proved to be a monumental flop and sadly his struggle at the Etihad Stadium seemed to mark the beginning of his demise as a top level footballer.

5. Guido Carrillo to Southampton

Guido Carrillo was brought in by Mauricio Pellegrino for £19m to save Southampton's 2017/18 season.

The towering centre-forward failed to score in 10 outings and twice went on loan to Spanish side Leganes before eventually moving to Elche on a free transfer.

4. Kostas Mitroglou to Fulham

Yet another striker brought in to save a club from relegation who unceremoniously flopped.

Kostas Mitroglou was signed by Fulham for £11m and played just 151 minutes without return as the Cottagers were relegated from the Premier League during the same season.

3. Juan Cuadrado to Chelsea

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There was little evidence on show to vindicate Chelsea's £23.3m swoop for Juan Cuadrado during his time at Stamford Bridge.

The Colombia international made just 15 appearances and spent time on loan at Juventus before finally signing a permanent contract with the Old Lady.

2. Savio Nsereko to West Ham

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Savio Nsereko was so bad that an unnamed teammate recently claimed "it felt like he had won a competition to play for West Ham."

The German winger signed from Brescia for £9m in 2009 and had left the east London outfit by the end of the summer window during the same year.

A story in 2012 suggested that he had faked his own kidnapping in an effort to extort money from his own family, though the player suggested his relatives had merely misunderstood a text message.

1. Alexis Sanchez to Manchester United

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Taking the least coveted of gold medals is transfer rebel Alexis Sanchez.

Sanchez shocked the world by snubbing Manchester City after a lengthy and well documented saga spanning more than six months and instead opting to join city rivals Manchester United in a swap deal involving Henrikh Mkhitaryan. 

Signing a contract worth a reported £450,000-per-week, there was an expectation that the Chilean could restore United to their former glory with his dynamic and relentless style of attacking midfield play. 

It turned out to be one of the most financially draining mistakes of the modern era as Sanchez stuttered and stagnated at Old Trafford, eventually joining Inter Milan on a free transfer in September 2020.