It has never really been the norm for English players to head abroad at the same rate stars from other countries do.
In the past few years, though, that has started to change. More young English upstarts are realising game time is more readily available abroad along with less pressure from the British press.
The latest arrival looks set to be Chelsea’s Ruben Loftus-Cheek. The English midfielder is due to join AC Milan following a breakthrough in talks for a relative snip due to his contract at Stamford Bridge expiring in 2024.
With that in mind, which other English players have played for Milan in the past and how did they get on?
Jimmy Greaves ended his career as the highest goalscorer in English top-flight football history with 357 goals and was also part of the Three Lions squad that won the 1966 World Cup.
Before he went to Tottenham, Greaves joined AC Milan for £80,000 in 1961. He signed a three-year contract but it went wrong before he had even arrived, deciding he wanted to stay in London as Milan refused to annul the deal.
He scored nine times in 13 games but left just a few months later with his morale extremely low and his relationship with coach Nereo Rocco broken.
More than 20 years went by before another English player turned out for AC Milan, but he only lasted slightly longer than Greaves. Luther Blissett arrived after being the First Division top scorer with Watford the season before.
He could not replicate that form when he arrived in Italy in the summer of 1983 and he only managed six goals in 39 appearances for the Rossoneri.
Blissett headed back to Watford after one season at Milan.
The first spell from an English player that lasted more than one year at AC Milan belongs to two old stars, the first being Mark Hateley. He spent three seasons with Milan, scoring 21 times in 86 games.
Hateley famously netted a winner in the Derby della Madonnina against Inter to earn Milan their first victory over Inter in six years.
He had a star-studded time in Italy, living above Ayrton Senna in his apartment block and playing five-a-side with the Formula 1 legend. Former tennis player Boris Becker also lived next door.
At the exact same time as Hateley, Ray Wilkins swapped Manchester United for AC Milan. He was quick to talk about the step up in physical fitness in Serie A, being more game-ready for the Rossoneri than with any other club in his career.
Wilkins was an important midfielder for Milan right up until the final few months of his spell but played while the team was struggling both on and off of the pitch.
He played 105 times for the Diavolo, scoring three times.
Another large chunk of time would go by before any other English players pitched up at AC Milan, and it was back to another short spell.
David Beckham was loaned from LA Galaxy to Milan in 2009 for six months, arriving in January. The deal was later extended until the end of the Serie A season, meaning the England legend missed the start of the MLS season.
He was effectively time-shared by the two clubs, something barely seen before at that level of football.
Beckham was steady if unspectacular for Milan. The Italian club wanted to sign him permanently but couldn’t find an agreement with LA Galaxy.
The only current English player in the AC Milan squad, trendsetter Fikayo Tomori has inspired others to make the move to Serie A.
He joined the Rossoneri when he had fallen out of favour at Chelsea and did not want to get stuck in the loan system again.
Almost as soon as he joined Milan, Tomori became a really important player and that only intensified when Simon Kjaer picked up a serious injury. He is coming into his third full season with Milan now, having won the Serie A title in the 2021/22 campaign and made over 100 appearances.
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