Trent Alexander-Arnold is reportedly set to leave Liverpool to join Real Madrid after his contract expires at the end of the season.

There have been a few massive Bosman moves over the years, and Alexander-Arnold would be the biggest ever to leave a Premier League club. Also, If he actually pens down to a move to Los Blancos, he would definitely replace an old teammate as the biggest in the Reds' Premier League record.

In this article, we explore the biggest free transfer exits for each of the 20 Premier League clubs.

Read Also | Trent to Real Madrid: Is it a done deal? Or is It just another rumor spreading?

Arsenal: Aaron Ramsey

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Following eight long years at the North London club, Aaron Ramsey departed Arsenal on a free transfer in July 2019 to sign for Juventus.

Ramsey's departure was disappointing but no one could question him; the wages Juventus offered him were astronomical.

Aston Villa: Thomas Hitzlsperger

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Thomas Hitzlsperger, renowned as 'Der Hammer', departed Aston Villa to change sides with VfB Stuttgart in July 2005 on a free transfer.

However, he returned to England five years later, signing with West Ham United in July 2010 and spending most of 2012/13 at Everton.

Bournemouth: Jefferson Lerma

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Even though Lerma's exit was hardly convenient for Bournemouth in the build-up to returning to the top flight, it was a huge loss for them.

He was a key figure in the Cherries' midfield and has proved to be an inspirational free transfer recruit for Crystal Palace in July 2023.

Brentford: Christian Eriksen

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The former Tottenham Hotspur midfield maestro was forced out of Serie A following his cardiac arrest at Euro 2020 and Brentford gave him a return to the Premier League, which was absolutely ideal in all respects.

Though he was desperate to retain him beyond the six-month deal he signed in January 2022, Brentford were unable to persuade Eriksen to put pen to paper, and the midfielder joined Manchester United.

Brighton: Jose Izquierdo

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Jose Izquierdo departed Brighton to join Club Brugge in the Summer of 2021 on a free transfer.

The Colombian winger's stay in Belgium, however, was brief, as he retired in 2022 soon after being released by Brugge.

Chelsea: Antonio Rudiger

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Thiago Silva, Andreas Christensen, Willian, Joe Cole, Michael Ballack, N'Golo Kante, Hernan Crespo, Nicolas Anelka, Andriy Shevchenko… Chelsea have a long list in this context to choose from.

Missing out on a top Antonio Rudiger would have hurt, though. The German centre-back was at Stamford Bridge for five years before he was roped in by Real Madrid in the Summer of 2022.

Crystal Palace: Wilfried Zaha

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Zaha is undoubtedly Palace's all-time best player. He departed when his deal ran out in the summer of 2023, signing for Turkish giants Galatasaray in a bold switch for Champions League action.

After years of transfer rumors that had him joining Arsenal, Zaha failed to sparkle in Turkey and was sent out on loan to French club Lyon after one season. That did not quite work out either, and he is now playing for Charlotte FC in the MLS.

Everton: Wayne Rooney

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Not the first time, as that was for a transfer fee, but the second time, Wayne Rooney departed Everton is likely their biggest Bosman loss of the Premier League era.

Rooney netted a staggering ten goals in 30 league games in 2017/18. His departure from Goodison Park was not only felt, but his arrival in America to play for D.C. United was shocking as well.

Fulham: Tosin Adarabioyo

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Fulham messed up by allowing Moussa Dembele to move to Celtic, but that is a regret rather than a huge transfer. Tosin Adarabioyo departed the Cottagers for London rivals Chelsea in the summer of last year, during his peak years.

Ipswich: Sylvain Legwinski

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Sylvain Legwinski, a former French midfielder, left Ipswich Town following the 2007/08 season and did not join a club until April of the following year before having a couple of months at St. Neots Town.

Leicester City: Youri Tielemans

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Caglar Soyuncu was a tragic loss, but nothing is close to Tielemans' departure at the end of the 2022/23 season.

The Belgian departed a club legend, having left with his FA Cup final goal in 2021. He was reportedly linked to Arsenal for ages before ending up with Aston Villa. Having had a struggling first year with Unai Emery, Tielemans is once again one of the top midfielders in the Premier League.

Liverpool: Georginio Wijnaldum

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Liverpool lost Wijnaldum to Paris Saint-Germain in a 2021 summer transfer window that also saw the signings of Lionel Messi, Gianluigi Donnarumma, and Sergio Ramos. It is little wonder that Wijnaldum's signing was overshadowed.

Manchester City: Ilkay Gundogan

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Alongside Erling Haaland and KDB, Gundogan was likely City's most crucial player in their Treble-winning 2022/23 season, with his final task as City captain being to hold aloft the Champions League trophy.

But after a year at his dream destination, Barcelona, the German midfielder renewed his connection to City, signing for the club in 2024.

Manchester United: Paul Pogba

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Pogba's experience at Manchester United was marred by debate. On His Day, he was a world beater. For the Red Devils' misfortune, he was quite literally only ever On His Day for France.

The best part of it all is that Man United let Pogba join Juventus for nothing in 2012, re-signed him for a world-record £89 million four years later, and then let him join Juventus for another free transfer in 2022.

Newcastle United: Jonas Gutierrez

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Gutierrez's departure in 2015 was typical of what Newcastle were like under Mike Ashley's ownership.

The Argentine preserved the Magpies in the Premier League after returning to the squad after suffering from cancer and wound up being let go over the telephone by John Carver.

Nottingham Forest: Stuart Pearce

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Following being at the club for 12 years, Pearce left on a Bosman move in 1997.

It was a miserable last season for Pearce, who took caretaker player-manager duties after Frank Clark's resignation. The job eventually shared with Dave Bassett, Forest slipped and a 35-year-old Pearce desired to be released, whereupon he became Newcastle United.

Southampton: Stuart Armstrong

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Stuart Armstrong departed from Southampton on a free transfer in September 2024 and signed for the Vancouver Whitecaps.

His contract at Southampton had run out at an earlier stage that summer. He was then signed as a Designated Player by the Whitecaps.

Tottenham Hotspur: Sol Campbell

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The greatest free transfer in Premier League history. The 'Big Sol' called an unexpected press conference, revealing his incredible transfer from Spurs to Arsenal in 2001, leaving everyone in sheer shock.

Campbell had already informed fans that he was remaining but rejected the opportunity to become the Spurs' best-paid player to achieve his ambition of playing in the Champions League. There was nothing to suggest Arsenal were even in the running for his signature, but stunned reporters watched the sensational and iconic unveiling.

Campbell went on to become an Arsenal legend and an integral part of the Arsenal Invicibles.

West Ham: Ben Johnson

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West Ham lost their academy gem, defender Ben Johnson, to Ipswich Town on a free transfer in July 2024.

Wolves: Adama Traore

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The Adama's future was the subject for ages' worth of talk. Spurs were in the running for a while, and most expected a switch to a big club when his Wolves deal ran out in 2023. Unfortunately, he signed for Fulham.

Wolves might have received a reasonable price for the Spanish midfielder but were unfortunate to lose him on a free transfer.

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