Six of the worst transfer deadline day moves in Premier League history

It’s that time of the year once again, with clubs up and down the land scrambling around to finalise their last pieces of transfer business, hoping to find that player who can impact the final few months of the season.

Supporters will be eagerly awaiting any news of potential arrivals and departures, deadline day having evolved into one of the most hotly-anticipated events on the football calendar.

However, while there have been some absolutely cracking deadline day deals over the years, not every piece of last-minute Premier League business has worked out so well.


Here are six of the worst transfer deadline day deals in Premier League history.

Andy van der Meyde

Inter Milan to Everton, 2005

Having just guided Everton to a top-four finish, David Moyes was desperate to strengthen his squad as the club prepared for Champions League football.

The Merseysiders secured an £8m deal for Inter Milan winger Andy van der Meyde, a Dutch international who had previously shone in an Ajax side containing the likes of Zlatan Ibrahimovic and Rafael van der Vaart.

The move proved to be a disaster however, injuries and off-field problems hampering Van der Meyde’s career at Goodison Park, with a red card in his first Merseyside derby against Liverpool a particular low point.

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In four seasons he made just 20 league appearances, alcohol issues and personal problems curtailing a once-promising career.

Afonso Alves

Heerenveen to Middlesbrough, 2008

Middlesbrough were struggling to avoid relegation in 2008 and in a desperate search for goals, secured the signing of Brazil international Alves from Dutch side Heerenveen.

Alves had been prolific in the Eredivisie, scoring 45 goals in just 39 league appearances before his £10m move to Teesside. The signing was eagerly anticipated, but the forward struggled to adapt to English football.

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He scored just 10 Premier League goals in two seasons at ‘Boro before leaving for Al-Sadd, the club relegated to the Championship at the end of his second campaign.

Paul Konchesky

Fulham to Liverpool, 2010

A player who moved for a relatively modest fee, but one whose transfer was perhaps one of the least popular in Liverpool‘s recent history.

Roy Hodgson had arrived at Anfield in 2010, his own appointment equally unpopular, and with the club in the midst of a dark period of ownership under American duo Tom Hicks and George Gillett, transfer recruitment was limited.

Hodgson decided to bring full-back Konchesky with him from Fulham, though the move proved a huge failure. The left-back failed to impress, whilst his mother’s decision to brand the club’s fans as ‘Scouse scum’ after criticism of his displays proved to be wholly unwise.

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After just 18 appearances he was deemed surplus to requirements, being sent on loan to Championship club Nottingham Forest.

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Fernando Torres

Liverpool to Chelsea, 2011

The Spanish striker had established himself as one of Europe’s finest forwards during a prolific three-and-a-half-year spell at Anfield, with Chelsea breaking the British transfer record to sign Torres from their Premier League rivals in January 2011.

Torres had scored 65 goals in just 102 league appearances for Liverpool, but having struggled towards the end of his time on Merseyside his fortunes only worsened at Stamford Bridge.

It took him 903 minutes to open his Chelsea account and he never reached double figures for league goals in any of the seasons he spent in west London.

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Despite his personal struggles he did achieve team success and won elusive silverware, winning an FA Cup and Champions League double in 2012.

Looking a shadow of the player who terrorised defences in the red of Liverpool, he was loaned out to AC Milan and Atletico Madrid before joining the latter permanently in 2016.

Andy Carroll

Newcastle to Liverpool, 2011

The aforementioned Torres transfer saw Liverpool desperately seeking attacking reinforcements, their search taking them to Newcastle to sign giant Geordie Andy Carroll.

The towering forward had helped fire Newcastle to promotion the previous season and adapted seamlessly to the top flight, hitting 11 goals across the first half of the Premier League campaign.

That form persuaded Liverpool to splash a club-record £35m to bring Carroll to Anfield, though the forward struggled following his big-money move.

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Injuries hampered his progress, whilst he seemed ill-suited to new manager Brendan Rodgers’ methods after the Northern Irishman replaced Kenny Dalglish.

After just 11 goals in 58 appearances, Carroll left the club to join West Ham and is currently a free agent following his release by former side Newcastle in 2021.

Kostas Mitroglou

Olympiakos to Fulham, 2014

A club-record signing, the Greek forward arrived at Fulham on deadline day in January 2014 for a fee of £12m.

Mitroglou had forged a reputation as a prolific goal scorer at Olympiakos, winning four league titles and scoring 81 goals in just 182 appearances for the club.

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The move proved to be a major flop however, Mitroglou struggling with fitness issues and making just three appearances for the Cottagers.

Fulham were relegated at the end of the season, with the Greek international swiftly heading back to Olympiakos on loan without scoring a single goal for the club.

Read: Five of the most iconic goal celebrations in Premier League history: Cantona, Klinsmann, Fowler

See also: Five great Premier League players who flopped as managers

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