Quiz! Can you name the 50 biggest transfers ever in football?
We're looking for the 50 most expensive footballers who have ever lived – how many do you remember?
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Football quiz time – and this is a fun one.
QUIZ Can you tell us whether each of these players have won the Ballon d'Or?
Over 100 years ago, Sydney Puddefoot was the most expensive footballer of all time. He cost Falkirk an outrageous £5,000 and earned himself a £390 fee for agreeing the transfer (he was also a cricketer for Essex… ah, the 1920s). "When will this folly on the part of football clubs come to an end?" The Football Post exasperatedly cried at the time. It was silly money. And it was only going to get worse.
It took just a month for Syd's fee to be surpassed, before the likes of Warney Cresswell, Bob Kelly, David Jack, Johnny Morris and Eddie Quigley all broke the record – and those are just the English players for under 30 grand. Diego Maradona broke it twice. Johan Cruyff did, too. Ronaldo, Alan Shearer and Zinedine Zidane all took the record, too. Yet in 2023, none of these names are in the top 50 most expensive footballers on Earth. What the hell would The Football Post say? 10 minutes on the clock, 50 players to guess for this quiz.
Article continues belowHandpicked football quizzes we know you'll love
Whether your knowledge of the market is as sharp as a late-night deadline day deal or you’ve just suffered a record-breaking valuation blunder, the window for more trivia remains wide open. We’ve scouted a brand-new selection of hurdles to see if you can handle the pressure: all powered by Kwizly.
If you pride yourself on being a Premier League connoisseur, it's time to put your money where your mouth is. We're challenging you to name every player to score 20+ goals in a Premier League season, alongside a tricky task that asks you to sort these players by the number of appearances they made in the Premier League. It is a test of both clinical finishing and top-flight longevity that separates the one-season wonders from the true legends of the game.
For those who prefer their football with a bit more travel, we have two geography-heavy challenges waiting in the wings. You can try to name every club Newcastle United have ever played in Europe to prove your Magpie credentials, or fly across the Atlantic and see if you can name every MLS team. From the traditional powerhouses of the North East to the burgeoning franchises of North America, let’s see if your footballing IQ is truly world-class.
FourFourTwo’s Weekend Crossword 42, featuring clues on stars, centre-backs, and Scrabble head-scramblers, is the perfect way to sharpen your wits before the weekend kick-off. To ensure you're never caught offside by a pub quiz question, sign up for our daily newsletter for a morning briefing that keeps you in the loop. You can also secure your status as a terrace legend by joining The Club: our free membership portal where you can snag exclusive quiz hints, earn badges, and trade blows for the top spot on our global leaderboards.
The best features, fun and footballing quizzes, straight to your inbox every week.

Mark White is the Digital Content Editor at FourFourTwo. During his time on the brand, Mark has written three cover features on Mikel Arteta, Martin Odegaard and the Invincibles, and has written pieces on subjects ranging from Sir Bobby Robson’s time at Barcelona to the career of Robinho. An encyclopedia of football trivia and collector of shirts, he first joined the team back in 2020 as a staff writer.
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