Skip to main content
FourFourTwo FourFourTwo FOOTBALL NEWS, FEATURES, QUIZZES
Sign in
  • View Profile
  • Sign out
flag of UK
UK
flag of Australia
Australia
flag of US
US
flag of Canada
Canada
flag of 대한민국
대한민국
flag of Türkiye
Türkiye
  • Soccer Cleat Buying Guides
  • Newsletter
  • News
  • Video
  • Features
  • Quizzes
  • Clubs
  • More
    • Interviews
    • The Magazine Archive
    • Subscribe
    • Lists
    • How to watch
    • About
FourFourTwo Magazine
FourFourTwo Magazine
Why subscribe?
  • Fascinating feature articles, covering everything from grass-roots football to the international scene
  • 'ACCESS ALL AREAS' pass to exclusive interviews with the biggest and best names in the game!
From$29.99
Subscribe now
Trending
  • WATCH the UCL
  • Transfers
  • Interviews
  • Messi
  • Ronaldo
  • EPL
Recommended reading
Florian Wirtz signs for Liverpool
Stories Ranked! The 10 most expensive British transfers ever
Arsenal midfielder Declan Rice, May 2025
Quiz Quiz! Can you name every Premier League club's record sale?
Quiz Quiz! Can you name the five biggest transfer fees for every year of the 2000s?
Manchester United players applaud their fans after a 4-3 defeat at Brentford in the Premier League in May 2025.
Lists Manchester United Premier League defeats in 2024/25
Liverpool midfielder Florian Wirtz moved from Bayer Leverkusen earlier this month
Quiz Quiz! Can you name the biggest Premier League signing every summer since 2000?
BIRMINGHAM, ENGLAND - SEPTEMBER 16: Jay Stansfield of Birmingham City celebrates his first goal during the Sky Bet League One match between Birmingham City FC and Wrexham AFC at St Andrewís at Knighthead Park on September 16, 2024 in Birmingham, England. (Photo by Jacques Feeney/Offside/Offside via Getty Images)
Quiz Quiz! Can you name the 30 most expensive signings by Football League clubs?
Arsenal midfielder Declan Rice, May 2025
Quiz Quiz! Can you name the biggest signings of the 2020s so far?
  1. Features

The 10 worst Premier League deadline day deals

By Alasdair Mackenzie published 30 January 2019

When you purchase through links on our site, we may earn an affiliate commission. Here’s how it works.

Deadline disasters

Deadline disasters

You never really know what you’re going to get on deadline day – but hurried deals aren’t usually the best ones, as this lot proved.

From bizarre gambles and overpriced mistakes to established stars wildly underperforming, there have been all sorts of examples of moves going south over the years...

Page 1 of 11
Page 1 of 11
10. Eric Djemba-Djemba – Man United to Aston Villa, 2005 (£1.5m)

10. Eric Djemba-Djemba – Man United to Aston Villa, 2005 (£1.5m)

Manchester United fans famously joked that the midfielder was “so good they named him twice”. By the end, though, they weren't laughing.

The Cameroonian was awful in his 20 top-flight outings for the Old Trafford side, but nevertheless did enough to merit a move to Villa in January 2005.

David O’Leary couldn’t get a song out of the struggling player either and he was eventually sent on loan to Burnley after making just 11 appearances for the Birmingham club. His deal was eventually terminated at the end of the 2006/07 season, before he disappeared into obscurity.

Page 2 of 11
Page 2 of 11
9. Benni McCarthy – Blackburn to West Ham, 2010 (Undisc.)

9. Benni McCarthy – Blackburn to West Ham, 2010 (Undisc.)

To be fair to West Ham, they had no reason to suspect that this wouldn’t be a successful deal, given McCarthy’s track record of 52 goals in 140 Blackburn appearances on top of the Champions League winners’ medal he earned at Porto.

However, the Hammers ended up forking out £1.5 million to cancel the South African’s deal early, just 14 months after signing him, after he had failed to score any goals in 13 matches and regularly struggled with injury issues.

He ended up verbal jousting with Karren Brady, and later reflected: "She started throwing blows at me and I can step into the ring with anyone. I wasn’t going to stand there as she spanked me in public, so I hit back."

Page 3 of 11
Page 3 of 11
8. Andre Santos – Fenerbahce to Arsenal, 2011 (£6.2m)

8. Andre Santos – Fenerbahce to Arsenal, 2011 (£6.2m)

Arsenal fans were hoping Santos could follow a long line of iconic Brazilian attacking full-backs like Roberto Carlos, Cafu and Maicon when he was brought in from Fenerbahce in 2011.

As it turned out, his nationality appeared to be the only trait he shared with those greats during a rotten 18-month spell in north London, in which he was criticised not only for his poor performances, but for trying to swap shirts with ex-Gunners favourite Robin van Persie at half-time of their league meeting with Manchester United.

Santos was eventually sent back to Brazil with a loan to Gremio, before cutting ties completely at the end of his contract when he joined Flamengo.

Page 4 of 11
Page 4 of 11
7. Paul Konchesky – Fulham to Liverpool, 2010 (£3m)

7. Paul Konchesky – Fulham to Liverpool, 2010 (£3m)

Roy Hodgson’s 2010 summer transfer window was one to forget, and ended up costing him his job at Anfield after Konchesky had followed the likes of Christian Poulson, Danny Wilson and Milan Jovanovic through the door.

The left-back pulled on a red shirt just 18 times before being shipped off to Nottingham Forest in the Championship on loan once Kenny Dalglish replaced Hodgson.

He never played for Liverpool again, departing for Leicester in 2011 for £1.5 million, where he eventually went on to appear in the top flight once more.

Page 5 of 11
Page 5 of 11
6. Xisco – Deportivo La Coruna to Newcastle, 2008 (£5.7m)

6. Xisco – Deportivo La Coruna to Newcastle, 2008 (£5.7m)

Newcastle decided to add the promising Xisco to their bulging line-up of strikers that already included Michael Owen, Obafemi Martins and Mark Viduka, having seen him impress for Spain U21s and in La Liga.

Lo and behold, he couldn’t get a game ahead of the more established names and was eventually loaned back to Spain with Racing Santander, having barely featured as the Magpies were relegated in 2008/09.

Upon his return, he still couldn’t find a way into the first team and his contract was eventually ripped up in January 2013 following another loan, this time at Deportivo. He scored just once for Newcastle.

Page 6 of 11
Page 6 of 11
5. Afonso Alves – Heerenveen to Middlesbrough, 2008 (£10m)

5. Afonso Alves – Heerenveen to Middlesbrough, 2008 (£10m)

Middlesbrough needed goals as they battled the drop in 2007/08, and in Alves they'd secured a Brazil international who was banging in a goal a game in the Netherlands.

What could go wrong? Well, almost everything, it transpired. Boro did manage to stay up initially – capped with a stonking 8-1 win over Manchester City in which Alves plundered a hat-trick – but their striker's return of four goals in 31 league games the following season wasn’t enough to keep them up at the second time of asking.

In September 2009, they cut their losses and sent him to Al-Sadd in Qatar, where he remained until retiring in 2013.

Page 7 of 11
Page 7 of 11
4. Radamel Falcao – Monaco to Man United, 2014 (£6m)

4. Radamel Falcao – Monaco to Man United, 2014 (£6m)

After prolific spells with Porto and Atletico Madrid, Falcao’s arrival at United promised great things as he was added to an attacking roster that already boasted the likes of Robin van Persie, Angel Di Maria and Wayne Rooney.

However, the Colombian couldn’t get up and running, and his return of four goals in 29 games fell way below what had been hoped for and expected at Old Trafford.

The option to make the loan move permanent was therefore turned down and he went on to suffer similar problems at Chelsea, before returning to peak form once he left English football for Monaco.

Page 8 of 11
Page 8 of 11
3. Chris Samba – Anzhi Makhachkala to QPR, 2013 (£12.5m)

3. Chris Samba – Anzhi Makhachkala to QPR, 2013 (£12.5m)

Just a month after Harry Redknapp had complained “there are a lot of players at this club who earn far too much money”, the QPR boss sanctioned the £12.5 million signing of Chris Samba on a £100,000 per week salary.

What’s more, the Congolese centre-back did nothing to improve an awful Loftus Road side and a few months after his arrival he told supporters to “get over” his sky-high earnings after an awful display against Fulham.

After 10 games and one relegation, QPR sold him back to Anzhi for £12 million.

Page 9 of 11
Page 9 of 11
2. Andy Carroll – Newcastle to Liverpool, 2011 (£35m)

2. Andy Carroll – Newcastle to Liverpool, 2011 (£35m)

On a frantic deadline day, Liverpool signed Newcastle’s ponytailed striker Carroll to replace the departing Fernando Torres.

A combination of poor form and injury problems ensured that his time at Anfield wasn’t memorable, with the former England striker mustering 11 goals in 58 games over two-and-a-half campaigns.

He was sent to West Ham on loan at the start of the 2012/13 season, a move that became permanent the following summer for about half the fee that the Reds had shelled out for his signature.

Page 10 of 11
Page 10 of 11
1. Fernando Torres – Liverpool to Chelsea, 2011 (£51.5m)

1. Fernando Torres – Liverpool to Chelsea, 2011 (£51.5m)

Towards the end of his time at Liverpool, Torres was struggling with injury and confidence issues, which only worsened once he'd moved to Chelsea for an eye-watering fee.

After losing to his former club on his debut, the Spain international went 903 minutes and two months without scoring, and the strike which ended that run turned out to be his only goal of the season.

His plight continued in subsequent seasons, although it didn’t stop Chelsea enjoying a good run during his time at Stamford Bridge; Torres left the Blues with FA Cup, Champions League and Europa League winners’ medals. Unsurprisingly, Chelsea found it hard to find a buyer in 2014, with Milan eventually swooping before he returned to boyhood team Atletico Madrid.

Page 11 of 11
Page 11 of 11
Alasdair Mackenzie

Alasdair Mackenzie is a freelance journalist based in Rome, and a FourFourTwo contributor since 2015. When not pulling on the FFT shirt, he can be found at Reuters, The Times and the i. An Italophile since growing up on a diet of Football Italia on Channel 4, he now counts himself among thousands of fans sharing a passion for Ross County and Lazio. 

Read more
Florian Wirtz signs for Liverpool
Ranked! The 10 most expensive British transfers ever
Arsenal midfielder Declan Rice, May 2025
Quiz! Can you name every Premier League club's record sale?
Quiz! Can you name the five biggest transfer fees for every year of the 2000s?
Manchester United players applaud their fans after a 4-3 defeat at Brentford in the Premier League in May 2025.
Manchester United Premier League defeats in 2024/25
Liverpool midfielder Florian Wirtz moved from Bayer Leverkusen earlier this month
Quiz! Can you name the biggest Premier League signing every summer since 2000?
BIRMINGHAM, ENGLAND - SEPTEMBER 16: Jay Stansfield of Birmingham City celebrates his first goal during the Sky Bet League One match between Birmingham City FC and Wrexham AFC at St Andrewís at Knighthead Park on September 16, 2024 in Birmingham, England. (Photo by Jacques Feeney/Offside/Offside via Getty Images)
Quiz! Can you name the 30 most expensive signings by Football League clubs?
Latest in
Hannah Hampton pointing
‘Things like that just give me goosebumps!’ Lionesses goalkeeper Hannah Hampton applauded by former England star for filling Mary Earps vacancy
Chloe Kelly celebrates England's 2025 Euros triumph
Why Lionesses hero Chloe Kelly made public apology after England's European Championship trophy parade
Alexander Isak in Newcastle training
Newcastle lining up £120m double-deal to replace Alexander Isak with TWO players: report
Bryan Mbeumo in pre-season training with Manchester United
'I'm really, really demanding of myself - and my teammates': Bryan Mbeumo tells Manchester United players and Ruben Amorim what he expects of them
Arsenal manager Mikel Arteta
Arsenal to offload £35m star, with London rivals looking at move: report
Arne Slot, Manger of Liverpool, celebrates with the Premier League trophy trophy, as Liverpool are crowned the Champions of the Premier League for the 2024/25 Season, following the Premier League match between Liverpool FC and Crystal Palace FC at Anfield on May 25, 2025 in Liverpool, England.
Liverpool fighting rivals for wonderkid defender: report
Latest in Features
Hannah Hampton pointing
‘Things like that just give me goosebumps!’ Lionesses goalkeeper Hannah Hampton applauded by former England star for filling Mary Earps vacancy
Bryan Mbeumo in pre-season training with Manchester United
'I'm really, really demanding of myself - and my teammates': Bryan Mbeumo tells Manchester United players and Ruben Amorim what he expects of them
Nick Pope (R) and Aaron Ramsdale (L) were England's back-up goalkeepers at the 2022 FIFA World Cup
Newcastle United's Aaron Ramsdale pursuit means one thing as Eddie Howe calls time on three-year absence
Liverpool duo Mohamed Salah and Dominik Szoboszlai in action during pre-season
Yokohama FM v Liverpool live streams: How to watch pre-season friendly
Chloe Kelly holds the Euro 2025 trophy
Quiz! Can you name every English player to start a Euros final?
Oasis are currently back on the road and have embarked on huge shows in Cardiff, Manchester and London
Oasis 2025: The footballers and managers who’ve been to see reformed Manchester duo so far
LATEST ARTICLES
  1. Hannah Hampton pointing
    1
    ‘Things like that just give me goosebumps!’ Lionesses goalkeeper Hannah Hampton applauded by former England star for filling Mary Earps vacancy
  2. 2
    Yokohama FM v Liverpool live streams: How to watch pre-season friendly
  3. 3
    Why Lionesses hero Chloe Kelly made public apology after England's European Championship trophy parade
  4. 4
    Newcastle lining up £120m double-deal to replace Alexander Isak with TWO players: report
  5. 5
    'I'm really, really demanding of myself - and my teammates': Bryan Mbeumo tells Manchester United players and Ruben Amorim what he expects of them

FourFourTwo is part of Future US Inc, an international media group and leading digital publisher. Visit our corporate site.

  • Terms and conditions
  • Contact Future's experts
  • Privacy policy
  • Cookies policy
  • Accessibility statement
  • Careers
  • About FourFourTwo
  • Advertise with us
  • Worldwide
  • How to pitch to FourFourTwo

© Future US, Inc. Full 7th Floor, 130 West 42nd Street, New York, NY 10036.

Please login or signup to comment

Please wait...