The worst Premier League transfer from every January window

The January transfer window is upon us once again, and whilst it maybe isn’t quite the frenzy of the summer window, it has still produced some of the finest success stories, and flops, in Premier League transfer history.

Here, I have attempted to include who I believe to have been the worst signing in every January window since its inception during the 2002/03 season, including some dishonourable mentions along the way.

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Unfortunately, despite my best efforts, this list ended up being rather striker-heavy – but that isn’t a surprise. By the midway point of the season, teams are usually desperate to find the player whose goals will make or break their season, typically paying over the odds to get them.

If it tells you one thing, though, it’s that Premier League clubs should perhaps shy away from risky January moves or buying players purely off of form – as it doesn’t always end well. 

(Fees are taken from multiple sources, including Transfermarkt. Deals labelled CR represent ones that were Club Record fees at the time).

2003 – Robbie Fowler to Manchester City – £6m

Past his best, increasingly injury-prone and the product of a player who probably peaked too soon, Robbie Fowler’s disappointing move to Manchester City during the inaugural January window is first up.

Fowler wasn’t dreadful in Manchester, however. He scored 27 goals in 92 games under Kevin Keegan and Stuart Pearce – including strikes against Everton, Liverpool, Spurs, Arsenal and three against Manchester United.

But he would return to Liverpool in January of 2006 on a free transfer, with his three year spell at City not exactly representing value for money at £6m – or £300,000 per Premier League goal. 

2004 – Scott Parker to Chelsea – £13m

Whilst some transfers on this list will make you wince in disbelief that clubs thought some of these deals were good ideas, Scott Parker’s move to Chelsea certainly isn’t one of those.

By the winter of 2004, the then-23-year-old was at the peak of his powers, spearheading an ambitious Charlton side to the dizzy heights of the Champions League places under Alan Curbishley. Unsurprisingly, his tenacious tackling and ability to carry the ball caught the eye of Chelsea, who signed him for £13m.

Unfortunately for Parker, however, Chelsea not only had a phalanx of midfielders – including Claude Makélélé, Emmanuel Petit and Frank Lampard – but also a habit of hoovering up talent without much of a solution on how to utilise it. This generally resigned Parker to the bench, before he departed for Newcastle eighteen months later after just 15 league appearances.

Charlton went on to finish seventh, Parker wasted part of his prime and Chelsea made a £5m loss when selling him – fair to nobody was a winner here.

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2005 – Eric Djemba-Djemba to Aston Villa – £1.5m

Poor Eric Djemba-Djemba. Whether it’s a list of the biggest Premier League flops, Manchester United’s worst signings, failed wonderkids – he can never seem to get away, with his 2005 January move to Aston Villa landing him into yet another category.

After a failed period at Old Trafford, Djemba-Djemba sought pastures new and found Aston Villa as willing suitors for a man who had promised plenty at Nantes and on the international stage with Cameroon. But again he struggled to find his feet, playing just eleven times before embarking on a truly bizarre career.

After Villa panic bought, and subsequently sold Djemba-Djemba for free, he went on to play in Qatar, India, Denmark, Israel and Scotland, amongst others, before retiring in 2016. I’m sure he’ll have a book in him one day.

2006 – Georgios Samaras to Manchester City – £6m

If a player is booed by their own fans, or openly criticised by a fellow teammate for not working hard enough, you can probably guess that they weren’t the best acquisition for the club – and so it proved for Georgios Samaras.

Standing at six foot four, the Greek international blundered into England from Dutch club Heerenveen (more on them later), for a staggering £6m – a hell of a lot of money for a mid-noughties City whose talisman was Joey Barton.

A decent return of four league goals in his opening eleven games from January to season’s end looked promising for the Cityzens, but the same total in 35 games the following year left a lot to be desired. Samaras eventually moved to Celtic for a £4m loss on what City had paid just two-and-a-half years earlier, but looked far closer to his level.

2007 – Lee Dong-gook to Middlesbrough – Free transfer

It’s not often that a club signs a free transfer and still gets ripped off, but that certainly seems to have been the case with Lee Dong-gook’s time at Middlesbrough. 

The forward arrived in the winter of 07, and whilst he would have brought some South Korean fanfare with him, he failed to display the form he had shown in his homeland – scoring just twice in 29 games for Boro, with both coming in cup competitions against lower league opposition.

After eighteen months in the north-east, he returned to South Korea with Pohang Stealers and later Jeonbuk Motors – going on to net over 200 goals for the latter and achieve legendary status, before retiring at the age of 41.

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2008 – Afonso Alves to Middlesbrough – £12.5m (CR)

Sorry Boro fans, maybe January window forwards aren’t for you (see Rudy Gestede and Jordan Rhodes for more). 

Signing strikers from Holland is typically hit or miss in the Premier League anyway. Whilst Luis Suárez and Ruud Van Nistelrooy scored goals galore over here, the likes of Mateja Kežman and Vincent Jannsen were laughably bad – and they’re joined by Afonso Alves.

Prior to his move to the north-east, Alves had smashed home a staggering 45 goals in 39 games for Heerenveen in the Eredivisie, a number made all the more remarkable when you consider that De Superfriezen finished 5th in both 06/07 and 07/08. These numbers alerted then-Boro boss Gareth Southgate to his availability, as he looked for the goals required to keep them out of danger.

By the end of their ridiculous 8-1 thumping of Manchester City on the final day – in which Alves scored a hat-trick – his league total stood at six goals in eleven games, but five of those had come in two games against the Manchester clubs and his only full season exposed how out of his depth he truly was. 

Just four league goals followed in 2008/09, as Boro were eventually relegated to the Championship and Alves was shipped off to Al Sadd in Qatar.

2009 – El-Hadji Diouf to Blackburn Rovers – £1m

When you talk about players whose profile skyrocketed after a World Cup, not many names can come before that of El Hadji Diouf from 2002. Deemed a decent prospect at French club Lens in the early noughties, Diouf’s star rose highest after a Man of the Match display for Senegal against France in a 1-0 win, prompting an already interested Liverpool to sign the forward for around £10m.

But by January 2009, Diouf’s reputation in terms of a lack of talent on the field, and being a total lunatic off it, had sparked a trail towards journeyman status, with Sam Allardyce signing him for Blackburn. He went on to make 62 appearances for Rovers and scored just four goals, before his contract was terminated for some typically childish antics.

When returning from a loan spell at Rangers in May 2011, Diouf brought his SPL Winner’s medal to training and taunted the rest of the squad, as they geared up for a final day relegation showdown with Wolves. A truly distasteful man, who rarely showed the talent to defend himself.

2010 – Benni McCarthy to West Ham – £3.5m

Whilst I did try to limit the amount of strikers in this list, it’s hard not to include a player who is generally considered as the worst signing ever made by West Ham – and that takes some doing.

After pretty good spells with Blackburn and Porto – winning the Champions League with the latter – Benni McCarthy rocked up at West Ham in January 2010 after being linked with the club for many years.

They must have wished he stayed on the wish list, however, as McCarthy failed to have a single goal involvement in 14 games and was fined £200,000 for being overweight.

That went some way to paying back the £3.5m the Hammers flushed away in the first place, but they ended up having to pay the South African a further £1.5m just a year later to get rid of him! In a long line of disastrous Gold and Sullivan signings, this is perhaps the worst.

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2011 – Andy Carroll to Liverpool – £35m (CR)

I find it remarkable to think that the same recruitment team picked out Andy Carroll at the same time as Luis Suárez, but they did, and the diminutive genius of the Uruguayan was joined by a big lump of a man who has since admitted he wanted to fail his medical.

The move made the Gateshead native the most expensive British player of all time, the second-most expensive player playing for an English club – behind Fernando Torres, the man he replaced (who also wasn’t great) – and the eighth most expensive footballer ever. Given all that, Carroll made the worst possible start.

A thigh injury suffered at Newcastle kept him sidelined for the best part of six weeks after his arrival, with his only goals of the campaign coming in a 3-0 win over Manchester City in mid-April. The next season wasn’t much better, with Carroll managing just nine goals in 47 games, as it became apparent that Liverpool maybe hadn’t got the player they thought they were going to.

2012 – Kevin De Bruyne to Chelsea – £9m

The 2012 January window was a relatively successful/low risk window for many clubs, meaning poor signings were generally few and far between. As always, QPR splurged cash on big name signings like Djibril Cissé and Bobby Zamora, but they helped the club to stay up, whilst a Cissé further up north originally did well at Newcastle and fired them to Europe. 

So instead, we’ve picked Kevin De Bruyne – purely for the fact that Chelsea let this one get away, and it probably would have been better if they hadn’t got involved at all. 

Despite signing in January 2012, ‘KDB’ stayed at Genk until the summer before a season-long loan move to Werder Bremen for the 2012/13 campaign. Upon his return, he made just three Premier League appearances before being sold to Wolfsburg in January 2014 for £18m. Whilst Chelsea doubled their money, it was hardly a sum worth watching what the Belgian has become.

A record-breaking season with Die Wölfe convinced Manchester City to shell out £55m on the midfielder in 2015 – a move worth every penny. To add salt to the already sore wound of watching the one that got away lift eight trophies with a rival club, in City’s 3-1 win over the Blues this January, De Bruyne scored his fourth goal against Chelsea in the Premier League – the most by a former player. Ouch!

2013 – Danny Graham to Sunderland – £5m

Not every striker who has played in the Premier League has the goal scoring quality of an Alan Shearer, or the mesmeric hustle and bustle of a Sergio Agüero, but that doesn’t make them bad players. Danny Graham was an average goal scorer at Swansea in the top flight, having done well to climb the ladder before that. But his time at Sunderland will go down in history for the wrong reasons.

After thirteen goalless games, he was sent on an unsuccessful loan to Hull, before another temporary move to Middlesbrough, and again to Wolves. Then, 828 days after joining, Graham finally scored his first and only goal for Sunderland in a 2-0 victory against Everton. 

By 2016, he’d moved permanently to Blackburn, before bizarrely returning to Sunderland last summer on a free transfer where he is again yet to score. This means that after eight years, Graham has cost Sunderland £5m-per-goal. Absolutely horrifying stuff.

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2014 – Kostas Mitroglou to Fulham – £13.5m (CR)

Signing a striker in January, ay. The height of desperation most of the time, with clubs paying a premium price for a man to shoot them away from danger with goals that they’ve promised elsewhere – but it doesn’t always work like that.

One of the most well-known striker flops is Greek goal machine Kostas Mitroglou, who joined Fulham in 2014 following 14 goals in just twelve league games for Olympiakos, as well as three in the Champions League. 

But the dream was far from the reality. ‘Mitrogoal’ mustered just three goalless Premier League appearances between January and May, as Fulham tumbled down into the Championship and was never seen again down by the River Thames.

At least the next ‘Mitro’ they signed was more successful.

2015 – Wilfried Bony to Manchester City – £28m

When mentioning a list of poor buys from Holland earlier in this piece, Bony was omitted from it given his time at Swansea. But the Ivorian does land himself on this list after his big money move to Manchester City failed to yield the same results. 

Having bagged 26 goals in 54 games for the Swans in a goal-laden eighteen months in South Wales, Manchester City pushed the boat out to sign Bony for £28m to aid them in their pursuit of a third Premier League title – but he failed to deliver it.

Whilst Bony may have sent Swansea fans wild into a frenzy of Slade fandom, he rarely lit up the Etihad, scoring only six times in the league for the Citizens before he was shipped off on loan to Stoke, and eventually Swansea for just £11m. 

Dishonourable mentions go to Juan Cuadrado’s move to Chelsea, and Andrej Kramaric’s failed switch to Leicester.

2016 – Oumar Niasse to Everton – £13.5m

After two-and-a-half years at Everton – of which he’d spent 18 months struggling – Roberto Martinez was frantically trying to add firepower to his Everton squad in a quest to bring a much needed trophy to Goodison Park. However, he inadvertently managed to sign the worst player in Everton’s esteemed history, for an eye-watering £13.5m.

That man was Oumar Niasse – a striker who didn’t know where the net was, a footballer who didn’t know what the ball was, and a man who absolutely stunk the place out in the majority of his appearances in blue, none more so than his first Premier League start.

By the 18th minute of that match against Bournemouth, he had only had two touches of the ball. Once when taking kick-off to start the game, the second when kicking off again after Marc Pugh’s 9th minute equaliser. Whilst some will point towards a decent return of eight league goals during 17/18, they were some of the worst goals the competition has ever seen. Including a goal line tackle on Petr Čech, and one that skidded in off his arse against Watford. 

The man who Niasse replaced was also in contention, as Steve Naismith’s £10m to Norwich yielded just one Premier League goal, whilst Stoke’s £21m acquisition of Giannelli Imbula and Newcastle’s purchase of Henri Saivet were also considered.

2017 – Saido Berahino to Stoke City – £12m

In 2015, Saido Berahino was a name on everyone’s lips. He broke through at West Brom in 2013, scoring a hat-trick in the League Cup against Newport on his debut, before going on to score the winning goal in a memorable 2-1 win at Old Trafford. By the time Tottenham had a £15m bid rejected in August 2015, Berahino was coming off the back of a 20-goal season for the Baggies.

The problem for Stoke was that January 2017 was very different to the summer eighteen months prior. By then, Berahino hadn’t scored a goal for almost a year, and was on a downward spiral of which he would never return. Despite this, Stoke splashed £12m on the forward – less than half of what West Brom valued him at when they rejected Spurs’ bid.

Weight issues, a failed drugs test and a crippling lack of confidence led Berahino to score just five goals in 56 games for the Potters before his contract was terminated after a drink-driving offence in 2019.

He now plies his trade in Belgium with Charleroi – a real shame for a player who appeared to have the world at his feet.

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2018 – Alexis Sánchez to Manchester United – Swap

If you were told back in 2018 that Alexis Sánchez – who had notched over 100 goals and assists for Arsenal over the previous three-and-a-half-years – was going to be included in such a list, many would have been stunned. But as soon you offer an ageing player wages of up to £400,000-a-week, you’re walking on thin ice.

It appeared that for Sánchez, if you’re walking on ice, you might as well dance, as the Chilean put in some incredibly lacklustre displays in United red during his eighteen month spell at Old Trafford. After just 45 appearances and five goals, he was moved on to Inter Milan where he has been somewhat more effective.

Whilst Sánchez took his place due to the ludicrous wages involved in the deal, the likes of Guido Carrillo’s move to Southampton, or Everton’s double swoop of Cenk Tosun and Theo Walcott were also considered.

2019 – Denis Suárez to Arsenal – loan

This is one of those signings that, when reminded of, it makes you exclaim: ‘oh God yeah, I forgot they signed him!’, which seals Denis Suárez’s place as a bonafide January transfer flop.

Whilst he only signed on loan from Barcelona, Suárez was expected to make an impact at Unai Emery’s Arsenal having played under the Spaniard during their Europa League winning 2014-15 campaign at Sevilla. It didn’t transpire that way, however, as the 26-year-old was limited to just 95 minutes of action for the Gunners, costing the club £29,500-per minute on the field.

He returned to Spain that summer and swapped Catalonia for Galicia – with Celta Vigo spending around £12m on the midfielder who has made sixteen league appearances so far this term. With Emery also back in Spain with Villarreal – one of Suárez’s former clubs – you wouldn’t rule out another reunion one day.

2020 – Danny Drinkwater to Aston Villa – Loan

But taking the accolade as the most recent January transfer flop is Aston Villa loanee Danny Drinkwater, who endured a torrid time in the midlands last season. Whilst I could have included Villa’s £8.5m acquisition of Mbwana Samatta (who had ‘loaned to random Turkish club’ within 12 months written all over him), the fact Drinkwater flopped at two separate clubs last term sealed his fate.

After a poor spell at Burnley, Drinkwater was handed a lifeline by Villa manager Dean Smith in a bid to revitalise a wayward career – but if anything, it pushed the Englishman further into the wilderness. A wretched debut against Manchester City summed it up; at fault for the second goal, seen blowing for tugs when chasing Kevin De Bruyne for the third and fourth goal, before being subbed off as the Villans fell to a 6-1 loss.

He played just three more times for Villa after that, before being sent home from training for a headbutt on fellow teammate Jota – bringing to an end a disastrously poor move which hindered Drinkwater even further.

So, there we have it. The worst January transfer in Premier League history from every season since the window’s inception, but who would you have included? Be sure to let us know!

The Author

James Pendleton

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