Free transfer signings take place across the Premier League every single summer and typically they have the potential to offer some of the greatest value in the sport. Throughout the history of the top flight, there have been many blockbuster signings who joined their clubs without the requirement of a transfer fee.
Here we will look at the best Bosman signings in Premier League history featuring iconic stars and even controversial switches that some fans will never let loose from their memories.
James Milner

James Milner is perhaps one of the greatest professionals the sport has ever offered. Throughout his long career, he has been committed to delivering his absolute best for himself and his teammates, on and off the pitch. The 38-year-old is currently playing for Brighton and Hove Albion having joined them on a free transfer from Liverpool in 2023 although that was far from the most significant free move of his career.
Milner could help the South Coast side to a top-six finish this season, as they are priced at +200 by Bovada sports betting to do just that. However, that would barely break the surface of what he achieved at his former club. The club he built his richest legacy with, Liverpool, is one of the favourites at that site’s Premier League odds for this season, a position they commonly held during his time at Anfield, too. Their football betting offerings also extend to European football with future betting on the UEFA Champions League winner available. Again, they position Liverpool among the leading teams.
While the site offers a variety of markets on the English top flight and the UCL, it covers the wider world of football as well as many other sports. Odds on huge European leagues like La Liga EA Sports and the Serie A are available for example, and other global sports like basketball and tennis are heavily covered. Beyond that you’ll find they offer betting on any of Milner’s current or former associations, as well as practically any major sporting event on the planet.
Always a privilege to play for you and a pleasure to enjoy success with you.
Thanks for everything.
YNWA#oncearedalwaysared pic.twitter.com/c64h6gGZNK— James Milner (@JamesMilner) May 28, 2023
Milner joined Liverpool for free in 2015 and went on to win every trophy possible in eight years as vice-captain of the Reds. The English midfielder was expected to bring crucial experience to Anfield as he joined after winning numerous titles with Manchester City. However, hindsight is what has shown he was one of the greatest free transfers in the league’s history.
Nobody ever expected Milner to play an influential role in the club’s greatest era since the 1980s. However, he alongside Jordan Henderson served as a calm head with a relentless work ethic that allowed Liverpool’s incredible technical profiles like Mohamed Salah and Sadio Mane to excel.
Few free transfers in world football history can claim to have been crucial in winning an abundance of trophies like Milner was.
Sol Campbell

Sol Campbell was certainly the most controversial transfer that is featured within this list having moved between North London rivals Tottenham Hotspur and Arsenal. The Spurs fans have never forgiven Campbell for moving to their biggest rivals – and for no transfer fee – although he will have few regrets having won two Premier League titles and three FA Cups with Arsenal.
Campbell was most famously the key man at the back for the Arsenal side that went undefeated across the 2003/04 Premier League season. If he had decided against the move from Spurs back in 2001 then ‘The Invincibles’ may never have been, and individually he may have never established himself as one of the leading defenders in English history.
Ruud Gullit

Ruud Gullit is another player who moved to a Premier League club for free and was massively influential in improving the winning culture within the setup. The Dutchman joined Chelsea from Sampdoria in 1995 and arrived with a reputation for being one of the greatest midfielders on the planet at that time. In Gullit’s opening season in West London, he was one of the league’s standout players although he was unable to force an end to the team’s trophyless run which dated back to the 1970s.
The summer before his second campaign though he was appointed as player-manager of the team and it was from there he truly began to shape the future of the club. Gullit had an immediate impact as he led the team to an FA Cup victory in his first year in charge to end the club’s lengthy barren spell.
ON THIS DAY
Ruud Gullit signed for Chelsea (1995) 💙 pic.twitter.com/3FSQpk6LuF
— Chelsea Photos (@ChelseaInPhotos) May 31, 2024
Gullit also helped to establish Chelsea as a challenging Premier League team as opposed to the mid-table minnows that they were when he joined. The Blues finished in sixth and fourth place respectively under the former Ballon d’Or winner’s tutorship. If Chelsea had never opted to go in for the Dutchman for free, then they may have turned out to be a very different club in the modern day – perhaps one without numerous UEFA Champions League trophies in their cabinet.
All of the free transfers mentioned here were consistently impressive on the pitch for the clubs they joined and were crucially much-needed leaders at their new destinations. This trio are the very best Bosman additions that England’s top-flight clubs have ever completed.