Quiz! Can you name the most expensive Premier League signing of every season?

Chelsea Unveil New Signing Moises Caicedo poses alongside his mother at Chelsea Training Ground on August 14, 2023 in Cobham, England.
(Image credit: Darren Walsh/Chelsea FC via Getty Images)

10 minutes on the clock, 31 players to guess.

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THEN TRY Quiz! Can you name every player to score 25+ Premier League goals before the age of 23?

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Back in 1993, a few million pounds would be able to buy you the most expensive player that the league had ever seen.

Now, it won't buy you a right leg. The cost of football has risen with the cost of living, all right, as we've gone from the British transfer record being £5 million to its current all-time high of £115m.

Try explaining that one to your dad. Try explaining also the players who aren't on today's list. Thierry Henry, David Silva and Wayne Rooney all moved for a lot of money – but not quite enough to be the most expensive of a window.

31 seasons on from those early days, can you tell us who was?


Quiz! Can you name the top 20 Premier League transfer profits ever?

Quiz! Can you name the 25 biggest-spending clubs of the 2020s so far?

Quiz! Can you name the top 50 winter transfers ever?

Mark White
Content Editor

Mark White has been at on FourFourTwo since joining in January 2020, first as a staff writer before becoming content editor in 2023. An encyclopedia of football shirts and boots knowledge – both past and present – Mark has also represented FFT at both FA Cup and League Cup finals (though didn't receive a winners' medal on either occasion) and has written pieces for the mag ranging on subjects from Bobby Robson's season at Barcelona to Robinho's career. He has written cover features for the mag on Mikel Arteta and Martin Odegaard, and is assisted by his cat, Rosie, who has interned for the brand since lockdown.