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 agree to the Terms & Conditions and Privacy Policy and are aged 16 or over.

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?
  • 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
  • 🚨 De Zerbi to Spurs
  • 😬 Palmer 'unsettled' at Chelsea
  • Ronaldo
  • EPL
  • Interviews
  • Transfers
  • Messi
  1. Team

9 times clubs REALLY regretted letting a star join their rivals

Features
By Paul Sarahs published 16 January 2018

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

"Taxi to Manchester..."

"Taxi to Manchester..."

Oh Arsenal, not again: If reports are to be believed, Alexis Sanchez looks all set for a Manchester United move this week. That would mean him following Gael Clichy, Samir Nasri, Emmanuel Adebayor, Robin van Persie and Bacary Sagna, among others, up the West Coast Main Line from Euston to Piccadilly.

But it's not just Arsenal sending their goods north: plenty of clubs have handed their rivals a crown jewel. And while transfers are inevitable in football, it’s not always the right move from the selling club’s perspective. Here we take a look at what happened when these nine high-profile players moved to a direct rival.

Page 1 of 10
Page 1 of 10
Andy Cole (Newcastle to Manchester United, 1995)

Andy Cole (Newcastle to Manchester United, 1995)

In January 1995, Newcastle boss Kevin Keegan decided that he no longer wanted Andy Cole, the striker who'd scored 55 goals in 70 league matches for the Magpies. Cole had been a force of nature at the head of Keegan’s attack-happy side, but the manager believed that something had changed in his star man.

Tensions ran high between the pair when Keegan suggested Cole hadn't been training at an acceptable level – and then, in January 1995, Tyneside was rocked when Newcastle accepted an offer of £6m (plus Keith Gillespie) from Manchester United for Cole.

Cole went on to win five Premier League titles with United, while the Magpies never fully recovered from a spectacular capitulation during the 1995/96 season that allowed the Red Devils – and Cole – to triumph.

Page 2 of 10
Page 2 of 10
Ashley Cole (Arsenal to Chelsea, 2006)

Ashley Cole (Arsenal to Chelsea, 2006)

In September 2006, the two London giants agreed a swap deal that took Ashley Cole to Stamford Bridge, with William Gallas (and £5m) going in the other direction. It proved to be one of the most controversial Premier League transfers, with Chelsea eventually found guilty of tapping up the England defender - and fined by the FA.

A few months after the move, Cole released his autobiography in which he revealed the moment he nearly swerved off the road at hearing Arsenal’s £55k-per-week contract offer.

It was a transfer that defined the contrasting trajectories of the two clubs. Chelsea, bankrolled by Abramovich’s billions, had real pulling power, while Arsenal’s status among the Premier League’s elite was under threat despite the 2004 Double and 2005 FA Cup win. The animosity directed at Cole by Arsenal fans was legendary, but it did little to stop him as he became one of the world's finest left-backs and achieved his objective of “winning things” with the Blues. Arsenal, meanwhile, didn't win another trophy until 2014.

Page 3 of 10
Page 3 of 10
Roberto Baggio (Juventus to Milan, 1995)

Roberto Baggio (Juventus to Milan, 1995)

Winning the Scudetto in 1995 was the apex of Baggio’s stay at Juventus – but he didn’t hang around to celebrate. Instead, the Divine Ponytail became the crown jewel in Milan’s quest to become Italy’s best once again.

At 28, Baggio had enjoyed his finest years in Turin and Alessandro Del Piero was the emerging star, yet selling him to a direct rival was not ideal. Juve fans were furious at the decision, as Baggio was allowed to join Fabio Capello’s Milan for £6.8m.

Although he wasn't the undisputed superstar at Milan, the Rossoneri won the following Serie A title with the help of some crucial goals from Baggio.

Juve's regret at allowing Baggio to leave was short-lived: in Baggio's absence they got to experience the full potential of Del Piero, who guided them to Champions League glory in 1996 and the Serie A title two years later.

Page 4 of 10
Page 4 of 10
Johan Cruyff (Ajax to Feyenoord, 1983)

Johan Cruyff (Ajax to Feyenoord, 1983)

A bona fide legend at Ajax, Cruyff would have been forgiven for thinking he was untouchable in Amsterdam. He was 36 in the summer of 1983 and had just helped Ajax win the double, but the Amsterdammers dragged their feet over giving their greatest-ever player a new contract.

The man who'd shaped Ajax’s destiny as much as anyone was apoplectic. His response to the club he'd served so immaculately was an emphatic middle finger – by signing for their biggest rivals Feyenoord.

The Rotterdam giants had consistently underachieved in the decade after winning the league and UEFA Cup in 1974, but Cruyff helped them to their first title since, plus a KNVB Cup, and was named Dutch Player of the Year. His spat with Ajax was short-lived, though - he returned as coach and changed the game forever.

Page 5 of 10
Page 5 of 10
Luis Figo (Barcelona to Real Madrid, 2000)

Luis Figo (Barcelona to Real Madrid, 2000)

Feeling under-appreciated in Catalonia, Figo decided to up sticks and move to bitter rivals Real Madrid in a world-record £37m deal. It proved to be one of the most acrimonious transfers in the history of the game, culminating in Figo being bombarded with objects thrown from the crowd upon his return to the Camp Nou - including, infamously, a pig's head.

Figo’s arrival at the Bernabeu signalled the beginning of the Galactico era and Barça’s sense of betrayal was exacerbated when Figo won the Ballon d’Or in November 2000, largely for what he'd done in the Blaugrana of Barcelona.

Seven months later, he was lifting the Liga trophy in the white of Real Madrid. Zinedine Zidane soon joined the Portuguese at the Bernabeu as Madrid won the 2002 Champions League title, with Figo an influential figure throughout their campaign.

Barcelona didn’t win the league title again until 2005.

Page 6 of 10
Page 6 of 10
N’Golo Kante (Leicester to Chelsea, 2016)

N’Golo Kante (Leicester to Chelsea, 2016)

Leicester City and Chelsea are hardly the bitterest of rivals - but the context and repercussions of this deal are key. An oversimplified take on Kante and Leicester goes a little something like this: they were outstanding with him and hopeless for months following his departure.

Naturally, Chelsea were keen to rebuild under Antonio Conte after a dismal title defence – and believed Kante was a crucial piece of the jigsaw. Leicester needed to retain their best players if they were to put up a reasonable defence of their title, but were left powerless when Kante expressed a desire to leave. It was soon proved just how important he was, though, with the Foxes’ decline and Chelsea’s immediate domestic superiority.

Leicester failed to plug the Kante-sized hole in the centre of their midfield and, with the threat of relegation looming large, Ranieri paid the price. Leicester won 12 Premier League games all season and ended up 12th.

Page 7 of 10
Page 7 of 10
Andrea Pirlo (Milan to Juventus, 2011)

Andrea Pirlo (Milan to Juventus, 2011)

The idea that Pirlo, one of the finest midfielders to grace a football pitch in the history of the game, would be deemed surplus to requirements beggars belief, but that’s exactly what the powers at Milan thought in 2011.

The playmaker had been integral to Milan’s success in the 2000s, helping them to two Serie A titles and the Champions League twice but the Bianconeri were a club on the up. New Juve boss Antonio Conte took Pirlo to Turin, with a new stadium and a fantastic squad determined to reestablish Juve as Italy's top side. Pirlo helped them achieve exactly that, making 13 assists as the Bianconeri finished the 2011/12 league season unbeaten to clinch their first title in nine years.

Juventus went on to win four consecutive titles, with the peerless Pirlo at the heart of the team – all while Milan tumbled spectacularly into decline. CEO Adriano Galliani would eventually admit that allowing Pirlo to leave was his biggest mistake in football.

Page 8 of 10
Page 8 of 10
Robin van Persie (Arsenal to Manchester United, 2012)

Robin van Persie (Arsenal to Manchester United, 2012)

Arsenal’s business model has made them look like a selling club at times, having been powerless to prevent key players like Patrick Vieira, Thierry Henry and Cesc Fabregas from joining those clubs more predisposed to splashing the cash.

In 2011/12, Gunners captain Van Persie was the Premier League's 30-goal top scorer, bagging against 17 different league opponents – then announcing his intention to leave. A Juventus bid was deemed insufficient, but Manchester United's bigger offer obliged the Arsenal board to sell. They believed that £24m for a 29-year-old with a history of injury problems was good business, and Arsene Wenger felt the position was adequately covered with Olivier Giroud and Lukas Podolski.

Ferguson not only strengthened United but weakened Arsenal significantly - as well as preventing Manchester City boss Roberto Mancini from signing a player he'd courted all summer. It proved to be one final masterstroke from the United boss as the Dutchman score 26 goals and led United to their 20th league title. Arsenal, meanwhile, just sneaked into the top four.

Page 9 of 10
Page 9 of 10
Carlos Tevez (MSI/West Ham/Manchester United to Manchester City, 2009)

Carlos Tevez (MSI/West Ham/Manchester United to Manchester City, 2009)

Adored by fans after excelling in Manchester United's Champions League-winning 2007/08 campaign, the Argentine grew increasingly irritated when his efforts on the pitch didn't result in a permanent deal at the club. Tevez promptly signed for Manchester City and immediately took aim at Fergie. City, much to the delight of their supporters, took full advantage with the now infamous 'Welcome to Manchester' campaign.

Ferguson responded by saying that Tevez wasn't worth the money City paid for him. The Argentine rather disproved the thesis by scoring 52 goals in his first two seasons at the Etihad, but it was his third year in sky blue that sticks in the craw of United fans. After refusing to come on as a substitute in a Champions League game against Bayern Munich in 2011, the Argentinian was widely condemned. Priced out of a January move away from the Etihad with Milan interested, Tevez returned from his self-imposed five-month exile and played a pivotal role in City clinching their first title in 44 years.

Page 10 of 10
Page 10 of 10
Paul Sarahs
Latest in Team
Mikel Arteta, Manager of Arsenal, looks on during the Emirates FA Cup Quarter Final match between Southampton and Arsenal at St Mary's Stadium on April 04, 2026 in Southampton, England.
Team Everything Arsenal boss Mikel Arteta said after defeat to Southampton in the FA Cup
 
 
BARCELONA, SPAIN - APRIL 02: Alexia Putellas of FC Barcelona celebrates scoring her team's first goal during the UEFA Women's Champions League 2025/26 Quarter-finals Second Leg match between FC Barcelona and Real Madrid CF at Nou Camp on April 02, 2026 in Barcelona, ​​Spain.
Team Barcelona Femeni belong on football’s biggest stage – and the headliners proved it at Spotify Camp Nou
 
 
Thomas Tuchel, Head Coach of England, pose on the red carpet prior to the FIFA World Cup 2026 Official Draw at John F. Kennedy Center for the Performing Arts on December 05, 2025 in Washington, DC.
Team When is the England World Cup 2026 squad announced?
 
 
Mohamed Salah is leaving Liverpool this summer
Team Mohamed Salah situation tells you exactly where Liverpool are right now
 
 
Chelsea owner Todd Boehly
Team Chelsea handed surprising PSR verdict amid record-breaking £262m losses
 
 
Eddie Howe in the dugout for Newcastle United vs Sunderland
Team Newcastle United could be forced to sell star players amid potential financial punishment
 
 
Latest in Features
Jack Harrison of ACF Fiorentina during the Serie A match between ACF Fiorentina and Pisa SC at Artemio Franchi on February 23, 2026 in Florence, Italy.
Player Jack Harrison interview: New York to Florence, via Leeds and Liverpool, the winger speaks to Henry Winter about his well-stamped passport, Bielsa, NYC, and the future aged 29 and on loan at Fiorentina
 
 
BARCELONA, SPAIN - APRIL 02: Alexia Putellas of FC Barcelona celebrates scoring her team's first goal during the UEFA Women's Champions League 2025/26 Quarter-finals Second Leg match between FC Barcelona and Real Madrid CF at Nou Camp on April 02, 2026 in Barcelona, ​​Spain.
Team Barcelona Femeni belong on football’s biggest stage – and the headliners proved it at Spotify Camp Nou
 
 
Thomas Tuchel, Head Coach of England, pose on the red carpet prior to the FIFA World Cup 2026 Official Draw at John F. Kennedy Center for the Performing Arts on December 05, 2025 in Washington, DC.
Team When is the England World Cup 2026 squad announced?
 
 
TOPSHOT - England's goalkeeper Jordan Pickford reacts after stopping the penalty kick of Colombia's forward Carlos Bacca (rear C) during the penalty shoot-out of the Russia 2018 World Cup round of 16 football match between Colombia and England at the Spartak Stadium in Moscow on July 3, 2018. (Photo by FRANCK FIFE / AFP) / RESTRICTED TO EDITORIAL USE - NO MOBILE PUSH ALERTS/DOWNLOADS        (Photo credit should read FRANCK FIFE/AFP via Getty Images)
Competition World Cup 2026 penalty shootouts: Every nation's record from the spot
 
 
Italy goalkeeper Gianluigi Donnarumma
Competition The 10 best players who won't be at World Cup 2026
 
 
World Cup 2026 wall chart
Products & Kit World Cup 2026 wall chart: Download yours for Australian Eastern Standard Time kick-offs, for FREE!
 
 
LATEST ARTICLES
  1. Mikel Arteta, Manager of Arsenal, looks on during the Emirates FA Cup Quarter Final match between Southampton and Arsenal at St Mary's Stadium on April 04, 2026 in Southampton, England.
    1
    Everything Arsenal boss Mikel Arteta said after defeat to Southampton in the FA Cup
  2. 2
    Former Chelsea man explains how Moises Caicedo justifies his £115m price tag
  3. 3
    How to watch Atletico Madrid vs Barcelona: Streams and TV info
  4. 4
    How to watch Southampton vs Arsenal: Streams and TV info
  5. 5
    Aston Villa star Morgan Rogers on playing Champions League football

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...