Best players to have moved from Chelsea to AC Milan and vice versa

Over the years we have seen some amazing players who have moved from Chelsea to AC Milan and vice versa. Both the teams have enjoyed the company of some great players who have been able to forge their magic in the Italian league and the Premier league. With Christian Pulisic being set to join AC Milan, the relationship in terms of player transfer between the two clubs continue to flourish.

Here we make a list of players who have been involved in transfer business with each other, directly. Some of these players are called a legend of both the clubs and some have only shined for one. Lets take a look at the players who have managed to play for these behemoth clubs.

Also read about the Transfer News of Christian Pulisic.

Chelsea to AC Milan transfers and vice versa

The following players are the result of direct transfer business between Chelsea and AC Milan and these players have donned the jerseys of both the clubs.

Jimmy Greaves

The Englishman is regarded as one of the greatest English strikers to have ever played the game and was the first ever player to make the move from Chelsea to AC Milan. He was signed by AC Milan on a three-year contract in June 1961 for £80,000.

He didn't get on with Nereo Rocco, Milan's head coach at the time and wasn't given much freedom on the field. So after spending one year at the club he went to Tottenham Hotspur for £99,999, which was termed as an unusual fee.

Marcel Desailly

The french World Cup and Euro champion enjoyed long spells at both the clubs. He's the only player in the list to have played over 100 matches for both the clubs. He's considered as one of the greatest centre backs and defensive midfielders of all time.

He was forced into becoming a defensive midfielder because in Milan for the centre back spot he was competing against the likes of Baresi and Costacurta. Desailly made the move from AC Milan to Chelsea in 1998 for a reported fee of £4.6m. He also became the captain of Chelsea football club and won 6 major trophies with the Blues.

George Weah

George Weah, who is now a Liberian politician, has previously won the Ballon d'Or and FIFA World Player of the Year in 1995 playing for AC Milan. He is one of the greatest African footballers of all time.

Weah was signed by the Blues on a half-a-season loan from Milan under then Chelsea manager, Gianluca Vialli on 11 January 2000. In his short period of time at West London, he won a million Chelsea hearts by scoring important goals for the club.

Hernan Crespo

The Argentine was signed by Chelsea for a record £16.8m from Inter Milan and then in 2004 he was loaned to AC Milan by Jose Mourinho on Carlo Ancelotti's (Milan's then manager) request. In 2005 he got recalled by Chelsea and was a part of the league winning side in 2006.

 He then experienced another loan spell, this time with Inter Milan and then in 2008 after his contract expired, he was released by Chelsea. He was then signed by Crespo's former manager in Chelsea, Jose Mourinho on a one-year contract with Inter Milan.

Andriy Shevchenko

The Ukrainian striker was part of the AC Milan team which lost in the UCL final to Liverpool in 2006. The former Ballon d'Or winner is one of the highest goalscorers of AC Milan. His move to Chelsea was said to be influenced by former Chelsea owner Roman Abramovich. 

AC Milan wanted to keep Shevchenko for six more years but he signed a contract with Chelsea in the summer of 2006 for £30.8m, which was a club record transfer fee. He was then loaned back to AC Milan in 2008-09 season because he was deemed surplus to Chelsea's requirements.

Michael Essien

The Ghanaian midfielder played for many clubs but he lived his best years at West London only. He was signed from Lyon by Chelsea and has made 168 appearances for the Blues. He was also part of Chelsea's Champions league winning team of 2012 and was then signed a long loan deal with Real Madrid under Jose Mourinho.

After the expiration of his loan spell at Real Madrid he went from Chelsea to Milan and signed a one-and-a-half-year contract with the Italian side. He made only 20 appearances for Milan scoring no goals.

Fernando Torres

Torres is regarded as one of the best Premier League strikers of all time but it was due to his amazing run of form for Liverpool, not Chelsea. Chelsea signed Torres for an undisclosed fee of around £50m and made him the sixth most expensive footballer ever at the time.

Due to his bad form at Chelsea he was loaned to AC Milan for two years on 31 August 2014. It was almost decided that his move to Milan is gonna be deemed permanent but some days later he decided to join his boyhood club, Atlético Madrid. 

Olivier Giroud

The 2018 World winner with France was signed by the Blues from their North London rivals, Arsenal for an undisclosed fee. Giroud's time at the Stamford Bridge was not a remarkable one but he did win the Champions League in 2021 with Chelsea.

He signed for Milan after that season only and was instrumental in Milan's Scudetto win. Milan was able to pen the french striker down on a two-year contract and it seems like he adapted pretty well to the Italian League.

Players who've played for both AC Milan and Chelsea