Premier League: Most profitable signing from every transfer window includes Mac Allister to Brighton

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.
Summer 2002
Robbie Keane (Leeds to Tottenham)
Signed for £9,000,000
Sold to Liverpool for £20,600,000 (2008)
Profit: £11,600,000
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.
Winter 2003
Matthew Upson (Arsenal to Birmingham)
Signed for £1,400,000
Sold to West Ham for £10,800,000 (2007)
Profit: £9,400,000
It’s almost impossible not to immediately picture Upson’s goal against Germany at the 2010 World Cup. Right off the nose.
Summer 2003
Cristiano Ronaldo (Sporting to Manchester United)
Signed for £16,300,000
Sold to Real Madrid for £80,600,000 (2009)
Profit: £64,300,000
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 BenzemaMost assists in Real Madrid history:
1. Karim Benzema
2. Cristiano RonaldoBoth signed in the same summer.🔝⚪️ pic.twitter.com/3TK9MLlvRc
— Madrid Zone (@theMadridZone) June 4, 2023
Winter 2004
Liam Rosenior (Bristol City to Fulham)
Signed for £68,000
Sold to Reading for £1,600,000 (2007)
Profit: £1,532,000
When they say there is no value in the January transfer window, they mean this particular January transfer window.
Summer 2004
Robin van Persie (Feyenoord to Arsenal)
Signed for £3,800,000
Sold to Manchester United for £26,300,000 (2012)
Profit: £22,500,000
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.
Winter 2005
Dean Ashton (Crewe to Norwich)
Signed for £5,100,000
Sold to West Ham for £9,300,000 (2006)
Profit: £4,200,000
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.
Summer 2005
Darren Bent (Ipswich to Charlton)
Signed for £3,000,000
Sold to Tottenham for £21,300,000 (2007)
Profit: £18,300,000
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.
Winter 2006
David Bentley (Arsenal to Blackburn)
Signed for £1,500,000
Sold to Tottenham for £18,900,000 (2008)
Profit: £17,400,000
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.
Summer 2006
Dimitar Berbatov (Bayer Leverkusen to Tottenham)
Signed for £13,500,000
Sold to Manchester United for £32,700,000 (2008)
Profit: £19,200,000
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.
Winter 2007
Christopher Samba (Hertha Berlin to Blackburn)
Signed for £430,000
Sold to Anzhi Makhachkala for £12,000,000 (2012)
Profit: £11,570,000
Blackburn did well in this window, also signing Stephen Warnock, who was sold to Aston Villa for a nice £5.7m profit.
Summer 2007
Gareth Bale (Southampton to Tottenham)
Signed for £12,600,000
Sold to Real Madrid for £87,000,000 (2013)
Profit: £74,400,000
Wales. Golf. Madrid.
Winter 2008
Antonio Valencia (Villarreal to Wigan)
Signed for £1,700,000
Sold to Manchester United for £16,100,000
Profit: £14,400,000
Eventually earned the No. 7 shirt at Old Trafford before ditching it after failing to live up to the hype.
Summer 2008
Luka Modric (Dinamo Zagreb to Tottenham)
Signed for £19,300,000
Sold to Real Madrid for £30,100,000 (2012)
Profit: £10,800,000
Was voted La Liga’s worst signing of the season after one year in Madrid. Ha.
Winter 2009
Charles N’Zogbia (Newcastle to Wigan)
Signed for £5,500,000
Sold to Aston Villa for £9,300,000 (2011)
Profit: £3,800,000
Charles Insomnia. Come on. You thought it too.
Summer 2009
Kyle Walker (Sheffield United to Tottenham)
Signed for £5,000,000
Sold to Manchester City £45,400,000 (2017)
Profit: £40,400,000
Blimey, Spurs are pretty good at this. Levy in, anyone?
Winter 2010
Victor Moses (Crystal Palace to Wigan)
Signed for £2,500,000
Sold to Chelsea for £9,900,000 (2012)
Profit: £7,400,000
That is two pretty lacklustre winter windows in a row, isn’t it?
Summer 2010
Matt Doherty (Bohemians to Wolves)
Signed for £77,500
Sold to Tottenham for £14,400,000 (2020)
Profit: £14,322,500
What is it with Irish right-backs and being bargains for less than £100k?
Winter 2011
Luis Suarez (Ajax to Liverpool)
Signed for £22,800,000
Sold to Barcelona for £70,400,000 (2014)
Profit: £47,600,000
Was pretty decent for Liverpool. Had the best individual season in Premier League history.
Summer 2011
Thibaut Courtois (Genk to Chelsea)
Signed for £7,700,000
Sold to Real Madrid for £30,100,000 (2018)
Profit: £22,400,000
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.
Winter 2012
Kevin De Bruyne (Genk to Chelsea)
Signed for £6,800,000
Sold to Wolfsburg for £18,900,000 (2014)
Profit: £12,100,000
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.
Summer 2012
Eden Hazard (Lille to Chelsea)
Signed for £30,100,000
Sold to Real Madrid for £99,000,000 (2019)
Profit: £68,900,000
One of Chelsea’s best-ever players to Real Madrid’s worst-ever signing. Hazard was very fun to watch.
Winter 2013
Philippe Coutinho (Inter to Liverpool)
Signed for £11,900,000
Sold to Barcelona for £116,300,000 (2018)
Profit: £104,400,000
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.
Summer 2013
Wilfried Bony (Vitesse to Swansea)
Signed for £13,700,000
Sold to Manchester City for £27,800,000 (2015)
Profit: £14,100,000
A rare mistake from Manchester City, who thought they could replace Edin Dzeko with Bony.
Winter 2014
Kelechi Iheanacho (Taye Academy to Manchester City)
Signed for £944,000
Sold to Leicester for £23,700,000 (2017)
Profit: £22,756,000
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.
Summer 2014
Romelu Lukaku (Chelsea to Everton)
Signed for £30,400,000
Sold to Manchester United for £72,900,000 (2017)
Profit: £42,500,000
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.
Winter 2015
Michael Keane (Manchester United to Burnley)
Signed for £2,200,000
Sold to Everton for £24,500,000 (2017)
Profit: £22,300,000
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.
Summer 2015
Virgil van Dijk (Celtic to Southampton)
Signed for £13,500,000
Sold to Liverpool for £72,900,000 (2018)
Profit: £59,400,000
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.
Winter 2016
Ben Godfrey (York City to Norwich)
Signed for £2,500,000
Sold to Everton for £23,600,000 (2020)
Profit: £21,100,000
Norwich bloody City. They also signed James Maddison in this window, making a delicious £19.1m profit.
Summer 2016
Oleksandr Zinchenko (Ufa to Manchester City)
Signed for £1,900,000
Sold to Arsenal for £30,100,000 (2022)
Profit: £28,200,000
Zinchenko was one of the signings of the 2022/23 season; Man City made a massive profit but Arsenal still struck a bargain.
Winter 2017
Gabriel Jesus (Palmeiras to Manchester City)
Signed for £27,500,000
Sold to Arsenal for £44,900,000 (2022)
Profit: £17,400,000
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.
Summer 2017
Harry Maguire (Hull to Leicester)
Signed for £11,700,000
Sold to Manchester United for £74,800,000 (2019)
Profit: £63,100,000
The less said about this one the better.
Winter 2018
Dodi Lukebakio (Charleroi to Watford)
Signed for £4,300,000
Sold to Hertha BSC for £17,200,000 (2019)
Profit: £12,900,000
You are forgiven if you have not got a clue. He played one game for Watford; they lost 2-0.
Summer 2018
Diogo Jota (Atletico Madrid to Wolves)
Signed for £12,000,000
Sold to Liverpool for £38,400,000 (2020)
Profit: £26,400,000
Jota joined Liverpool out of the blue (and into the red) and has been a huge success under Jurgen Klopp.
Winter 2019
Alexis Mac Allister (Argentinos Juniors to Brighton)
Signed for £6,800,000
Sold to Liverpool for £35,000,000 (2023)
Profit: £28,200,000
Mac Allister has been officially announced by Liverpool. This profit should have been a whole lot bigger. The Reds have done extremely well here.
Summer 2019
Dan James (Swansea to Manchester United)
Signed for £15,300,000
Sold to Leeds for £25,000,000 (2021)
Profit: £9,700,000
How? Nobody knows. And how did he play so many games for Manchester United?
Winter 2020
Joao Pedro (Fluminense to Watford)
Signed for £9,900,000
Sold to Brighton for £29,400,000 (2023)
Profit: £19,500,000
Pedro will join up with his Brighton teammates for pre-season after becoming their record signing.
Summer 2020
Raphinha (Rennes to Leeds)
Signed for £16,000,000
Sold to Barcelona for £49,000,000
Profit: £33,000,000
A very good signing made by Leeds. Oh, how they could have used his individual quality this season.
Winter 2021
Ben Davies (Preston to Liverpool)
Signed for £1,500,000
Sold to Rangers for £4,000,000 (2022)
Profit: £2,500,000
Covid was a right bastard, eh? At least one good thing came from this utterly pointless transfer.
Summer 2021
Marc Cucurella (Getafe to Brighton)
Signed for £15,400,000
Sold to Chelsea for £56,100,000 (2022)
Profit: £40,700,000
Fair play to Brighton for this one, they have truly pulled Chelsea’s pants down.