Skip to main content
Join The Club
- Join our community
17
Member Features
24/7
Access Available
5K+
Active Members
Live Q&A Sessions
Weekly interactive sessions
Member Competitions
Win exclusive prizes
Exclusive Content
Premium articles & videos
Early Access
First to see new features
Exclusive Newsletters
Football news direct to your inbox
Monthly Rewards
Surprise gifts & perks
GET CLUB ACCESS QUICK
For the quickest way to join, simply enter your email below and get access. We will send a confirmation and sign you up to our newsletter to keep you updated on all your football news.
By submitting your information you agree to the Terms & Conditions and Privacy Policy and are aged 16 or over.
FIND OUT ABOUT OUR MAGAZINE
Want to subscribe to the magazine? Click the button below to find out more information.
Find out more
Get Club Access Quick

Join The Club for quick access. Enter your email below and we'll send confirmation plus sign you up to our newsletter.

By submitting your information, you confirm you are aged 16 or over, have read our Privacy Policy and agree to the Terms & Conditions. Geographical rules apply.

Background
Welcome to Fourfourtwo club !
Hi ,

Your membership journey starts here.

Keep exploring and earning more as a member.

MY ACCOUNT

Badge picture
Earn your first badge
Complete 1 quiz to unlock your first badge.
Keep earning badges
Explore ways to get more involved as a member.
Football Quizzes

Football Quizzes

Quick quizzes for football fans.

Read Now
Football Crosswords

Football Crosswords

Football-themed crossword challenges.

Read Now

See what you’ve unlocked.

Explore your membership benefits.

Explore
Member Exclusives
Find the subscription that suits you

Find the subscription that suits you

We’ve highlighted the subscriptions our members get the most value from.

Explore

Sign Out
FourFourTwo FourFourTwo FOOTBALL NEWS, FEATURES, QUIZZES
UK EditionUK AU EditionAustralia US EditionUS CA EditionCanada KR Edition대한민국 TR EditionTürkiye
Sign in
  • View Profile
  • Sign out
  • Soccer Cleat Buying Guides
  • Newsletter
  • News
  • Video
  • Features
  • Quizzes
  • Clubs
  • Membership
  • More
    • Interviews
    • Opinion
    • The Magazine Archive
    • Subscribe
    • How to Watch
    • About
    • Lists
FourFourTwo Magazine
FourFourTwo Magazine
Why subscribe?
  • Subscribe today and receive the World Cup preview issue for FREE
  • 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
Save 36%
Subscribe now
Trending
  • 🚨 New Arsenal kit
  • ✍️ Carrick contract offer
  • Ronaldo
  • EPL
  • Interviews
  • Transfers
  • Messi
  1. Competition
  2. Premier League

The 10 worst Premier League deadline day deals

Features
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. 

Latest in Competition
Heineken Oslo UWCL
Competition Heineken’s ‘Oslo’ Women's Champions League takeover in London
 
 
Liverpool hold the advantage going into the final day
Competition What happens if Bournemouth and Liverpool finish level on points, goal difference and goals scored?
 
 
Champions League Predictor
Competition FourFourTwo's Champions League Predictor: Predict the final and WIN
 
 
The Champions League trophy.
Competition Why won’t the Champions League final be free-to-air for the first time ever?
 
 
 Kevin Schade of Brentford (C) celebrates scoring his team's third goal during the Premier League match between Burnley and Brentford at Turf Moor on February 28, 2026 in Burnley, England.
Competition How many European places does the Premier League get?
 
 
BBC World Cup 2026 presenters, pundits, commentators and reporters
Competition World Cup 2026: The BBC's presenters, pundits, commentators and reporters in full
 
 
Latest in Features
Heineken Oslo UWCL
Competition Heineken’s ‘Oslo’ Women's Champions League takeover in London
 
 
Fans celebrate as Arsenal are confirmed as Premier League champions, as they gather outside the Emirates Stadium, on May 19, 2026 in London, England.
Quiz Quiz! Can you name every Arsenal player to have won the Premier League?
 
 
Champions League Predictor
Competition FourFourTwo's Champions League Predictor: Predict the final and WIN
 
 
David Mokwa Ntusu of SV Elversberg celebrates victory with the fans following the 2. Bundesliga match between SV 07 Elversberg and SC Preußen Münster at Ursapharm-Arena
Team Is this the smallest club ever to play in a major European league?
 
 
Pep Guardiola head coach of Manchester City and Spain celebrates the victory after winning the UEFA Champions League 2025/26 League Phase MD6 match between Real Madrid C.F. and Manchester City at Estadio Santiago Bernabeu on December 10, 2025 in Madrid, Spain. (Photo by Jose Breton/Pics Action/NurPhoto via Getty Images)
Coaches & Managers Who will Pep Guardiola manage next? The leading contenders to hire Manchester City head coach
 
 
The Champions League trophy.
Competition Why won’t the Champions League final be free-to-air for the first time ever?
 
 
LATEST ARTICLES
  1. Mikel Arteta has led Arsenal to the Premier League title
    1
    Arsenal make summer transfer plans to build around major contract extension: report
  2. 2
    World Cup 2026: ITV's presenters, pundits, commentators and reporters in full
  3. 3
    Quickfire Quiz 124: Can you answer 10 questions in 90 seconds?
  4. 4
    Inter Miami fan protest leads to tense exchange with Lionel Messi
  5. 5
    'If you went back to that kid, you’d see that he always believed in himself. He believed he was going to make it' Martin Odegaard exclusive: Arsenal's title-winning captain reflects on his journey to the Premier League

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

Add as a preferred source on Google Add as a preferred source on Google
  • 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...