The current transfer window system was introduced for the 2002/03 season, so that is where we are starting this whole journey.
The transfers here are from the window they were bought, not sold. We will use the €80m profit Chelsea made from Eden Hazard’s move to Real Madrid as an example. Hazard’s €35m switch to Stamford Bridge is credited to summer 2012, not the 2019 summer window when he left.
All deals are taken from Transfermarkt, who deal in euros, so every fee is converted using the current exchange rate – which is less than ideal – but the fact they are the most profitable player of that particular window still stands.
Robbie Keane (Leeds to Tottenham)
Signed for £9,000,000
Sold to Liverpool for £20,600,000 (2008)
Keane lasted a grand total of six months at Anfield after six years at White Hart Lane, returning to Spurs in February 2009 for a few quid less.
Matthew Upson (Arsenal to Birmingham)
Signed for £1,400,000
Sold to West Ham for £10,800,000 (2007)
It’s almost impossible not to immediately picture Upson’s goal against Germany at the 2010 World Cup. Right off the nose.
Cristiano Ronaldo (Sporting to Manchester United)
Signed for £16,300,000
Sold to Real Madrid for £80,600,000 (2009)
Won a Champions League, three Premier League titles, an FA Cup, and the Ballon d’Or before breaking the world transfer record to join Real Madrid, where he won a whole lot more and became their all-time leading goalscorer. It went quite well.
Most goals in Real Madrid history:
1. Cristiano Ronaldo
2. Karim Benzema
Most assists in Real Madrid history:
1. Karim Benzema
2. Cristiano Ronaldo
Both signed in the same summer.🔝⚪️ pic.twitter.com/3TK9MLlvRc
— Madrid Zone (@theMadridZone) June 4, 2023
Liam Rosenior (Bristol City to Fulham)
Signed for £68,000
Sold to Reading for £1,600,000 (2007)
When they say there is no value in the January transfer window, they mean this particular January transfer window.
Robin van Persie (Feyenoord to Arsenal)
Signed for £3,800,000
Sold to Manchester United for £26,300,000 (2012)
Couldn’t win diddly-squat at Arsenal so joined United, where he led them to the Premier League title in his first season, which was also Sir Alex Ferguson’s last.
Dean Ashton (Crewe to Norwich)
Signed for £5,100,000
Sold to West Ham for £9,300,000 (2006)
Norwich could not retain their Premier League status (it was ever thus) but they did make a tidy profit on the excellent but injury-prone striker.
Darren Bent (Ipswich to Charlton)
Signed for £3,000,000
Sold to Tottenham for £21,300,000 (2007)
Bent was a bit of a bagsman back in the day and helped Charlton earn a very tasty profit after his 13 goals could not prevent relegation.
David Bentley (Arsenal to Blackburn)
Signed for £1,500,000
Sold to Tottenham for £18,900,000 (2008)
From Bent to Bentley, the ex-Arsenal, Tottenham and Blackburn midfielder had a wand of a right foot but could not thrive at White Hart Lane.
Dimitar Berbatov (Bayer Leverkusen to Tottenham)
Signed for £13,500,000
Sold to Manchester United for £32,700,000 (2008)
Now, this is a bit of a sticky one. West Ham signed Carlos Tevez for £12.5m and then loaned him to Man United for £10.8m before selling him to Man City for £24.8m, meaning they earned £35.6m, which was £23.1m more than they bought him for. That is clearly more than the Berbatov profit but we have arbitrary rules and we are sticking with them.
Christopher Samba (Hertha Berlin to Blackburn)
Signed for £430,000
Sold to Anzhi Makhachkala for £12,000,000 (2012)
Blackburn did well in this window, also signing Stephen Warnock, who was sold to Aston Villa for a nice £5.7m profit.
Gareth Bale (Southampton to Tottenham)
Signed for £12,600,000
Sold to Real Madrid for £87,000,000 (2013)
Wales. Golf. Madrid.
Antonio Valencia (Villarreal to Wigan)
Signed for £1,700,000
Sold to Manchester United for £16,100,000
Eventually earned the No. 7 shirt at Old Trafford before ditching it after failing to live up to the hype.
Luka Modric (Dinamo Zagreb to Tottenham)
Signed for £19,300,000
Sold to Real Madrid for £30,100,000 (2012)
Was voted La Liga’s worst signing of the season after one year in Madrid. Ha.
Charles N’Zogbia (Newcastle to Wigan)
Signed for £5,500,000
Sold to Aston Villa for £9,300,000 (2011)
Charles Insomnia. Come on. You thought it too.
Kyle Walker (Sheffield United to Tottenham)
Signed for £5,000,000
Sold to Manchester City £45,400,000 (2017)
Blimey, Spurs are pretty good at this. Levy in, anyone?
Victor Moses (Crystal Palace to Wigan)
Signed for £2,500,000
Sold to Chelsea for £9,900,000 (2012)
That is two pretty lacklustre winter windows in a row, isn’t it?
Matt Doherty (Bohemians to Wolves)
Signed for £77,500
Sold to Tottenham for £14,400,000 (2020)
What is it with Irish right-backs and being bargains for less than £100k?
Luis Suarez (Ajax to Liverpool)
Signed for £22,800,000
Sold to Barcelona for £70,400,000 (2014)
Was pretty decent for Liverpool. Had the best individual season in Premier League history.
Thibaut Courtois (Genk to Chelsea)
Signed for £7,700,000
Sold to Real Madrid for £30,100,000 (2018)
Has established himself as the best goalkeeper in the world at Madrid. That Champions League final performance last year remains rent free in Liverpool fans’ heads.
Kevin De Bruyne (Genk to Chelsea)
Signed for £6,800,000
Sold to Wolfsburg for £18,900,000 (2014)
This may have been the biggest profit of the January 2012 window, but f**k me, don’t Chelsea regret this one?! Also, Genk to Chelsea is just lovely.
Eden Hazard (Lille to Chelsea)
Signed for £30,100,000
Sold to Real Madrid for £99,000,000 (2019)
One of Chelsea’s best-ever players to Real Madrid’s worst-ever signing. Hazard was very fun to watch.
Philippe Coutinho (Inter to Liverpool)
Signed for £11,900,000
Sold to Barcelona for £116,300,000 (2018)
The most profitable transfer of all time? The third-highest transfer fee ever paid was for Coutinho. It is fair to say he failed to justify it.
Wilfried Bony (Vitesse to Swansea)
Signed for £13,700,000
Sold to Manchester City for £27,800,000 (2015)
A rare mistake from Manchester City, who thought they could replace Edin Dzeko with Bony.
Kelechi Iheanacho (Taye Academy to Manchester City)
Signed for £944,000
Sold to Leicester for £23,700,000 (2017)
Kurt Zouma falls into the loan fee category having raked in £13.4m across two separate loan spells, but none of those were with West Ham, who helped Chelsea pick up a £17.5m profit from the transfer fee they paid Saint-Etienne. So we stick with Iheanacho.
Romelu Lukaku (Chelsea to Everton)
Signed for £30,400,000
Sold to Manchester United for £72,900,000 (2017)
Lukaku’s spell at Everton is by far his best in England. His 25 Premier League goal haul of 2016/17 remains his most prolific season.
Michael Keane (Manchester United to Burnley)
Signed for £2,200,000
Sold to Everton for £24,500,000 (2017)
Was great for Burnley. Has been pretty bad for Everton and shows no signs of improvement, even after being reunited by Sean Dyche. Great profit though.
Virgil van Dijk (Celtic to Southampton)
Signed for £13,500,000
Sold to Liverpool for £72,900,000 (2018)
Van Dijk transformed Liverpool into an absolute juggernaut, helping them reach the Champions League final after six months, only for Loris Karius to f**k everything up.
Ben Godfrey (York City to Norwich)
Signed for £2,500,000
Sold to Everton for £23,600,000 (2020)
Norwich bloody City. They also signed James Maddison in this window, making a delicious £19.1m profit.
Oleksandr Zinchenko (Ufa to Manchester City)
Signed for £1,900,000
Sold to Arsenal for £30,100,000 (2022)
Zinchenko was one of the signings of the 2022/23 season; Man City made a massive profit but Arsenal still struck a bargain.
Gabriel Jesus (Palmeiras to Manchester City)
Signed for £27,500,000
Sold to Arsenal for £44,900,000 (2022)
Both signings that made the Gunners title contenders feature here. Another current Arsenal player, Aaron Ramsdale, was the second-most profitable signing in this window, joining Bournemouth for less than £1m, three-and-a-half years before joining Sheffield United for around £17m.
Harry Maguire (Hull to Leicester)
Signed for £11,700,000
Sold to Manchester United for £74,800,000 (2019)
The less said about this one the better.
Dodi Lukebakio (Charleroi to Watford)
Signed for £4,300,000
Sold to Hertha BSC for £17,200,000 (2019)
You are forgiven if you have not got a clue. He played one game for Watford; they lost 2-0.
Diogo Jota (Atletico Madrid to Wolves)
Signed for £12,000,000
Sold to Liverpool for £38,400,000 (2020)
Jota joined Liverpool out of the blue (and into the red) and has been a huge success under Jurgen Klopp.
Alexis Mac Allister (Argentinos Juniors to Brighton)
Signed for £6,800,000
Sold to Liverpool for £35,000,000 (2023)
Mac Allister has been officially announced by Liverpool. This profit should have been a whole lot bigger. The Reds have done extremely well here.
Dan James (Swansea to Manchester United)
Signed for £15,300,000
Sold to Leeds for £25,000,000 (2021)
How? Nobody knows. And how did he play so many games for Manchester United?
Joao Pedro (Fluminense to Watford)
Signed for £9,900,000
Sold to Brighton for £29,400,000 (2023)
Pedro will join up with his Brighton teammates for pre-season after becoming their record signing.
Raphinha (Rennes to Leeds)
Signed for £16,000,000
Sold to Barcelona for £49,000,000
A very good signing made by Leeds. Oh, how they could have used his individual quality this season.
Ben Davies (Preston to Liverpool)
Signed for £1,500,000
Sold to Rangers for £4,000,000 (2022)
Covid was a right bastard, eh? At least one good thing came from this utterly pointless transfer.
Marc Cucurella (Getafe to Brighton)
Signed for £15,400,000
Sold to Chelsea for £56,100,000 (2022)
Fair play to Brighton for this one, they have truly pulled Chelsea’s pants down.