The 10 Worst January Signings in Premier League History (Ranked)

The 10 Worst January Signings in Premier League History (Ranked)

The January transfer window: you can’t live with it, and you can’t live without it. Just as football fans think they’ve left a summer of transfer rumour mayhem, the January window gives them a good old-fashioned slap in the face to bring them back to reality.

The rumour mills are spinning, big targets are hinting, and clubs across the country are yearning for a New Year’s upgrade that helps them achieve their competitive ambition for the season.

However, in the past, the winter window has proven itself to be hugely changeable. Some years, every move ends up a success, while in other years, fans find themselves thinking, “What was the point in that signing then?” So, having covered the best January signings in Premier League history, it is now time to examine the worst.

10. Alexandre Pato to Chelsea From Corinthians – Six-Month Loan (2016)

Once one of Europe’s brightest, most promising young names, Alexandre Pato’s limelight had faded considerably by the time he got to Stamford Bridge. Injuries had cut his time at AC Milan short, and in a bid to return to his best, he had moved back to his native Brazil, playing for both Corinthians and Sao Paulo.

However, it quickly became clear that he was not the same player that once graced the pitch at the San Siro - despite joining in the midst of a catastrophic title defence, Pato did little to convince Jose Mourinho that he deserved a place in the team, making just two appearances in six months.

Pato🗣️:

“When I arrived at Chelsea, Diego Costa was the number 9. The press were criticising him, the fans were swearing, yet he always remained calm. I asked him, ‘How do you cope with all this pressure?’ He replied, ‘Pato, I don’t understand anything. I don’t speak English.”😅 pic.twitter.com/rWzKcwlO3w

— Players Sayings (@PlayersSayings) August 12, 2025

He did score on debut against Aston Villa, a cool, collected penalty, but his lack of minutes and unconvincing showings had fans thanking their lucky stars that it was just a loan deal.

9. Kim Kallstrom to Arsenal from Spartak Moscow – Six-Month Loan (2014)

It’s another loan, and get used to them, because they appear a number of times throughout this list. This time, Arsenal were the club to make a fool of themselves, signing the Swedish international despite the midfielder nursing a severe back injury at the time.

Six years ago he walked in, took a penalty, won a trophy and then walked out again.

The strange story of Kim Kallstrom's Arsenal career, told by the man himself...

📕 The Guy With The Broken Back

— Arsenal (@Arsenal) April 12, 2020

He made just three appearances for the Gunners, failing to score or assist, and unsurprisingly, Arsene Wenger did not make his deal a permanent one. Though Kallstrom made the French and Russian top flights look like child's play with Rennes, Lyon and Spartak Moscow, his Premier League opportunity simply found him at the wrong time.

8. Cenk Tosun to Everton from Besiktas - £27 million (2018)

The first non-loan deal of the list, Tosun was brought to Everton after scoring for fun in the Turkish top flight, where he scored 80 goals in just over 200 appearances for the likes of Gaziantepspor and Besiktas. However, the Turkish international quickly found out the Premier League was a different beast altogether.

It took him two months to open his account for the club against Burnley, but he did manage a further four in the last two months of the season. However, four goals in 29 games the next season, and just one more over the following two saw him shipped back to Besiktas, first on loan, and then on a permanent deal.

BREAKING: @Everton sign Cenk Tosun for £27m from Besiktas on a four-and-a-half year deal. #SSN pic.twitter.com/gVYgGl1BJc

— Sky Sports News (@SkySportsNews) January 5, 2018

Tosun now plies his trade for Fenerbahçe, where he has two goals in 29 appearances.

7. Juan Cuadrado to Chelsea from Fiorentina - £23.3 million (2015)

A second Chelsea entry on the list (and not the last), Cuadrado arrived at the Blues from Fiorentina just six months after he dazzled with Colombia at the 2014 World Cup. Alongside James Rodriguez, he had helped drag his nation all the way to the quarter-finals, and despite being knocked out by Brazil, the winger came away from the tournament with plenty of credit.

Mo Salah has scored 6 goals since his move to Fiorentina - a deal that saw Juan Cuadrado move to Chelsea. #SSNHQ pic.twitter.com/Ic89puQNsP

— Sky Sports News (@SkySportsNews) March 6, 2015

However, his Chelsea career never got out of first gear - of his 14 games that season, Cuadrado started just four and assisted once as Chelsea romped to the title, and after one appearance the next season, he was shipped out to Juventus on loan. Twice in fact, before his move to Turin was made permanent in 2017.

6. Jean Kevin-Augustin to Leeds United from RB Leipzig - £40 million

Signed on loan with an initial £17.7 million option to buy in the summer of 2020, nobody was to know that Augustin would go down as one of the worst value-for-money signings in Premier League history. Augustin played 48 minutes across three games, suffered a muscle injury, and left at the end of the season when his loan deal had expired.

However, Leeds’ promotion meant they had to trigger the permanent buy option, which they subsequently appealed, claiming that the COVID-extended season “nullified” the deal. However, their appeal was unsuccessful, and meant they had to pay Leipzig the full fee for Augustin, although the player did not actually join the club.

On this day in 2020… 🗓️

Leeds signed Jean-Kevin Augustin!

One of the worst transfers in the history of football…

👉 He joined on loan with an obligation to buy for £18 million

👉 Played just 48 minutes

👉 Leeds tried to cancel the permanent transfer

👉 RB Leipzig took… pic.twitter.com/1x3uR2AJWv

— Second Tier podcast (@secondtierpod) January 27, 2025

Worse still, Leeds then had to stump up a further £24.5 million for a breach of contract, bringing their total outlay on Augustin to just over £40 million. In all, Augustin cost the Whites around £13,715 per second in a Leeds shirt. Truly shambolic.

5. Kostantinos Mitroglou to Fulham from Olympiakos - £12 million (2014)

Joining the Cottagers as their record transfer in a bid to stave off relegation, the Greek forward held the hopes of every Fulham fan on his meaty shoulders. Having scored 37 goals across the last season and a half in his home country, Craven thought he could prove to be one of the bargains of the year.

Steve Sidwell on his time at Fulham with Kostas Mitroglou 🗣 "This fucker, he did not stop eating. He was a big boy. Every time you saw him, he'd be walking round the training ground with a fucking protein bar." pic.twitter.com/VOZCDv6YfM

— Footy Accumulators (@FootyAccums) September 12, 2019

However, it ended up looking like one of the biggest wastes of money of all time. Accused by Steve Sidwell that he “never stopped f****** eating”, Mitroglou made just three goalless appearances for the club as they were comfortably relegated at the end of the season. Remarkably, Fulham managed to recoup half of what they spent on him, no mean feat when his pure incompetence up front was given closer scrutiny.

4. Lewis Grabban to Bournemouth from Norwich City - £8 million (2016)

One of the most bizarre entries on this list alongside Augustin, Grabban was initially viewed as a Cherries hero, as he netted 35 goals in 91 games as the club shot up to the Championship, despite being signed for a mere £300,000. Sold for £3 million when Eddie Howe decided to beef up his attack in a bid to reach the Premier League, it appeared Grabban’s Bournemouth days were behind him.

However, after a less than middling 13 goals in 44 games for Norwich City, Howe ridiculously saw fit to part with £8 million to bring him back to the Vitality Stadium, giving him his first ever Premier League minutes.

Watford (A) in 2014/15…

Watford 0-3 Norwich City

⚽️ [65’] Lewis Grabban
⚽️ [70’] Cameron Jerome
⚽️ [85’] Lewis Grabban#NCFC

pic.twitter.com/OsKJWHYxN1

— Norwich City Updates (@norwich_updates) December 6, 2025

Needless to say, it was a catastrophe - Grabban played 22 times and scored just one goal before being shipped out to Reading, Sunderland and Aston Villa on loan. Bournemouth eventually sold him to Nottingham Forest in 2018 for £6 million, ending the nightmare.

3. Mykhailo Mudryk to Chelsea from Shakhtar Donetsk - £62 million (2023)

The most recent move on this list, and certainly the most expensive, Mudryk’s time at Chelsea so far has been … eventful. When he was signed in January 2023, Chelsea thought they had pipped Arsenal to the next big thing, and Mudryk’s debut against Liverpool reinforced that; he was direct, confident and absolutely rapid, and looked like money well spent.

A very big thank you to @ChelseaFC for signing mudryk. Without you guys, we wouldn't have signed Leonado trossard from Brighton https://t.co/vsF9vvPlH0

— Hb²⁴🥷 (@johnhublot24) January 2, 2026

However, he quickly lost confidence, failed to score until October, netted a total of 10 goals in 73 games, and is now banned for four years after failing a drugs test in December of 2024. His cost per game currently sits at just under £1 million, and going by the fact he hasn’t played a game in over a year, that figure doesn’t look like it’s going to get better any time soon.

2. Savio Nsereko to West Ham from Brescia - £9 million (2009)

Brought in as West Ham’s record signing after being named in the 2008 U19 Euro’s Team of the Tournament, the German, who could play anywhere across the frontline, looked to be the perfect complimentary partner for Carlton Cole as the Hammers looked to stay up.

However, having scored just three goals in 22 games for a second-tier Italian side, very few were caught by surprise when Nsereko flopped. Failing to score, and assisting just one in 10 appearances for the Hammers, he was sold on to Fiorentina at the end of the season, as his side survived relegation by the skin of their teeth.

Actually happening lol, now it’s down to the coin flip of whether he turns out to be Neymar Jr or Savio Nsereko https://t.co/vHVlkdq8nF

— morg (@29morg) June 8, 2024

It was not the only time Nsereko was the source of controversy - while on loan at 1860 Munich, he disappeared for a week, eventually being found at his sister’s place, while later, in 2016, he faked his own kidnapping in an attempt to extort his family while on holiday in Thailand.

1. Alexis Sanchez to Manchester United from Arsenal - Swap Deal + £30 million (2018)

The king of the failed January move, Alexis Sanchez’ move to Manchester United has gone down in history for all the wrong reasons. United looked like they had bartered their way to a world beater when they fobbed off Henrikh Mkhitaryan to Arsenal in return for the Chilean, but in fact, it was Arsenal who got the marginally better deal.

He played 45 times for the Red Devils, scored just five times, and looked incredibly uncomfortable in his new setting despite his eye-watering wages topping £500,000 per week. He did at one point score against his former club in a cup game, but this was nowhere near enough to justify his salary, and after just a season and a half, he was allowed to leave for Inter Milan on a free transfer, where he would never regain the outrageous form he found at Arsenal.

Alexis Sanchez will forever regret leaving Arsenal for Manchester United. pic.twitter.com/wS09hFeCoK

— Nekstylez (@Nekstylez) December 26, 2025

Mkhitaryan, meanwhile, had a little more success, netting nine times and assisting 12 in one and a half seasons at the Gunners before joining Roma, also on a free transfer. The two would actually reunite at Inter Milan at the start of the 2023/24 season.