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

The Premier League has seen some of the greatest figures who have led their respective teams to ultimate glory, wearing the captain's armband. These players have been monumental in shaping the clubs' history or writing the golden chapters the clubs have enjoyed over the years, in the past or now. 

The captain's armband carries a significant value and thus it deserves the players who lead the core from the front as a true leader. This list includes some of those footballers who have not only captained their sides to innumerable glories but also set examples for the upcoming generations. 

Sportz Point ranks these five footballers based on collected achievements and the long-standing impact they have created on their respective clubs as well. 

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Terry, Gerrard, Vieira, Keane and Kompany: Ranking the Greatest Premier League Captains

5. Vincent Kompany – Man City

Vincent Kompany cemented his legend at Manchester City when he captained the club to their inaugural Premier League title in the 2011/2012 season.

The Belgian center-back was among the limited number of players who stayed at City following the takeover by Sheikh Mansour in 2008, having signed for the club prior to the takeover being completed. During his time at City, Kompany led the team to four Premier League titles, with his last championship win being in the 2018/2019 season.

10 - Since Vincent Kompany's first season with the club, @ManCity have won more domestic trophies than any other side in England (4 Premier League titles, 4 League Cups, 2 FA Cups). Era. pic.twitter.com/DOGcPOYFyy

— OptaJoe (@OptaJoe) May 19, 2019

His exceptional leadership and defensive abilities made him a true icon of the club. This is reflected in his impressive Premier League record, consisting of 265 appearances, 18 goals, 8 assists, and 94 clean sheets.

4. Steven Gerrard – Liverpool

Steven Gerrard is practically synonymous with Liverpool. Despite not winning any Premier League title as a captain, the 'Captain Fantastic' Gerrard solidified the spirit of the club by leading by example through his remarkable talent, determination, and commendable attitude.

He famously inspired Liverpool to a comeback victory in the 2005 UEFA Champions League final with a heroic performance, cementing his place in Anfield folklore as one of the greatest captains in the history of the club.

540 Games
120 Goals
92 Assists

Steven Gerrard is the latest player to be inducted into the @premierleague’s Hall of Fame.

LEGEND 👏 pic.twitter.com/NDYZrRX3yZ

— ESPN UK (@ESPNUK) May 20, 2021

Gerrard's record in the Premier League is impressive as well, with 504 games, 120 goals, and 92 assists, and this further cements his place as a Liverpool legend.

3. Patrick Vieira – Arsenal

Patrick Vieira was a very crucial part of the Arsenal team during all three of their Premier League victories. He served as club captain for the triumphs in the 2001-02 and 2003-04 seasons. The latter season featured the famous Arsenal Invincibles, who completed the entire league campaign without losing a single match.

Patrick Vieira arrived at Arsenal in 1996, the same time Arsene Wenger did. Next season, they won the double.

He captained Arsenal’s ‘Invincibles’ side. His final kick in Arsenal colors won the FA Cup.

He returns today as Crystal Palace manager and as an Arsenal legend 🔴 pic.twitter.com/dFCCLKjVUW

— B/R Football (@brfootball) October 18, 2021

Vieira is considered one of the best footballers in his position and is also one of the most successful and respected captains of the Premier League. 

2. John Terry – Chelsea

John Terry is one of the all-time greats in the history of the Premier League. Appointed Chelsea captain by Jose Mourinho in 2004, Terry took the Blues to their maiden Premier League crown in the same year.

🔹 5x Premier League winner
🔹 5x FA Cup winner
🔹 3x League Cup winner
🔹 Champions League winner
🔹 Europa League winner

24 years ago today, John Terry began his legendary Chelsea career 🏆 pic.twitter.com/TYwvs34Qaz

— B/R Football (@brfootball) October 28, 2022

During his 12 years as Chelsea captain, Terry had a very successful career winning five FA Cups, three League Cups, the Europa League, and the 2012 Champions League. In the Premier League, he played 492 times and scored 41 league goals, becoming the highest-scoring defender in Premier League history till date.

1. Roy Keane – Manchester United

Roy Keane is widely regarded as the Premier League's all-time greatest captain. Joined with intense drive and masterful leadership, Keane led Manchester United to four Premier League titles and the legendary treble of 1999. His unstoppable courage, tireless work ethic, and leadership through example made him an all-time Manchester United icon.

Roy Keane is the most decorated Irish player in Premier League history, winning seven league titles with Manchester United. pic.twitter.com/cybzycAhcs

— The Extreme Football Enthusiast (@ExtremeFootbal4) March 13, 2025

Keane's Premier League career further reinforces his legacy. He played 366 games, scored 39 goals, and won 220 matches, suffering just 61 losses during his time. Keane's incredible story goes beyond the Premier League years, however, and shows how his legacy has lasted for a long time.

Keane's stay at the Old Trafford, however, came to a sudden end following a falling out with manager Sir Alex Ferguson in 2005.

Carabao Cup, formerly known as the EFL Cup, is a 92-team knock-out tournament organised by the English Football League (EFL). Teams from Premier League, and three divisions of the English Football League compete in this tournament.

Although the prize value of the EFL Cup is not that significant compared to tournaments like FA Cup and other, EFL Cup has had it's reputation among football fans since 1961. Here are all the previous winners of the Carabao Cup since the beginning.

Who were the first-ever winners of the Carabao Cup?

Aston Villa were the first-ever champions of the Carabao Cup or the EFL Cup in 1961. They defeated Rotherham United by a 3-2 aggregate after a two-leged final after being down by 0-2 in the first leg. Alan O'Neill, Harry Burrows and Peter McParland were the scorers for Aston Villa.

For the first six seasons, the EFL Cup finals were played in two legs.

Who are the current winners of the Carabao Cup?

Newcastle United defeated defending champions Liverpool FC at Wembley Stadium to win their maiden EFL Cup or Carabao Cup title. They defeated Liverpool by 2-1 to clinch their first-ever domestic title since 1955 FA Cup triumph.

Alexander Isak and Dan Burn scored the goals for them.

𝐂.𝐇.𝐀.𝐌.𝐏.𝐈.𝐎.𝐍.𝐒 🏆

Newcastle United lift a domestic title for the first time in 70 years!

They beat Liverpool FC to clinch the Carabao Cup 2024-25!

Congrats, Newcastle United!#NewcastleUnited #CarabaoCupFinal #CarabaoCup #LiverpoolFC pic.twitter.com/RUfDu2zNhj

— Sportz Point (@sportz_point) March 16, 2025

Also Read: Most Goals in the Premier League for a single club

Which is the most successful team in Carabao Cup history?

Liverpool with 10 EFL trophies, are the most successful team in Carabao Cup history. They won the trophy in 1980-81, 1981-82, 1982-83, 1983-84, 1994-95, 2000-01, 2002-03, 2011-12, 2021-22, and 2023-24 seasons.

Most successful teams in Carabao Cup/ EFL Cup history

Most Carabao Cup wins as a player

Sergio Aguero and Fernandinho are the most successful players with three Carabao Cup titles in 2014, 2016, 2018-2021 with Manchester City.

All the past winners of the Carabao Cup/ EFL Cup since 1961

Hello and welcome to another live coverage of Premier League football. This evening, we will bring you all the live updates, scores, news, and free commentary of the high-intense Arsenal vs Chelsea Premier League 2024-25 fixture set to be played at the Emirates Stadium in London.

Arsenal are currently placed second on the table, having earned 55 points in 28 matches. On the other hand, Chelsea are now standing in the fourth position with 49 points in 28 games.

Both teams are having a good season so far, but the result of this match will either benefit or put pressure on other teams competing in the top-four race. So sit back and enjoy the game as we bring you all the real-time updates, team news, live scores, and match commentary tonight.

This is Soumit Bhattacharya, who will bring you all the updates of the match from the web desk.

Moreover, you can follow us on Twitter for all the updates. Join our Telegram and WhatsApp channels to get all the news and scores.

Hello and welcome to another live coverage of Premier League football. This evening, we will bring you all the live updates, scores, news, and free commentary of the Manchester City vs Brighton Premier League 2024-25 fixture set to be played at the Etihad Stadium in Manchester.

Manchester City, the defending champions, are having a difficult season and are currently battling to secure a spot in continental competitions for next season. The Cityzens are now standing in the fifth position, having earned 47 points in 28 matches. On the other hand, Brighton are just one point behind City, positioned seventh as of now with 46 points in 28 games.

Although City is struggling, this encounter against Brighton will be crucial for both teams before heading onto the international break. So sit back and enjoy the game as we bring you all the real-time updates, team news, live scores, and match commentary tonight.

This is Soumit Bhattacharya, who will bring you all the updates of the match from the web desk.

Moreover, you can follow us on Twitter for all the updates. Join our Telegram and WhatsApp channels to get all the news and scores.

AC Milan have reportedly finalized the decision to part ways with current manager Sergio Conceicao following the end of the ongoing season.

According to multiple reports from Italy, the Portuguese manager can also be shown the door if the Rossoneris fail to earn victories against in their upcoming two matches against Lecce and Como, which are scheduled to take place before the international break in March.

Despite winning the Supercoppa Italiana with AC Milan in January, while beating the eternal rivals Inter Milan in the final, Conceicao failed to lead Milan to the coveted success in Serie A this season. 

Conceicao to bow out of Milan at the season's end

According to Italian journalist Nicolo Schira, Conceicao's tenure at AC Milan "will be over at the end of the season". With another looming threat over the 50-year-old, he could lose his job as early as this month, if Milan suffers defeats against Lecce and Como before the international break.

#ACMilan have decided not to confirm Sergio #Conceicao. His story at #Milan will be over at the end of the season, even if he could be sacked with the immediate effect if he loses against Lecce and Como before the international break. #transfers

— Nicolò Schira (@NicoSchira) March 8, 2025

Corriere della Sera, another well-known Italian media outlet, reported that Milan may consider dismissing head coach Conceicao before the summer clause takes effect. This would allow both parties to part ways 'early' if the team's performance does not improve in the coming week.

The pressure is now mounting on Sergio Conceicao as AC Milan is currently positioned ninth on the Serie A leaderboard, having accumulated 41 points across 27 games. 

During the summer, Conceicao was already a top candidate for the head coach position at Milan. However, the club ultimately chose Paulo Fonseca for the role. After a few months of disappointing results, Fonseca was dismissed, and his compatriot Conceicao took over as the new head coach.

The former FC Porto manager took charge of AC Milan on 30 December 2024. Under his managerial radar, the Rossoneris have played 17 matches, achieving 8 wins, 3 draws, and 6 losses so far.

Conceicao's tussle with Arrigo Sacchi

Sergio Conceicao's stay at Milan has been distressing due to the continuous speculations from different discussions. Recently, the Portuguese manager has been heavily criticized by the legendary former Milan coach Arrigo Sacchi, who "feels that it is ‘complicated’ for Conceicao to salvage his job in San Siro".

In his La Gazzetta dello Sport column, Sacchi conveyed his belief that it is "complicated" for Conceicao to save his job at San Siro. He also believes that the main issue is the lack of unity among the squad, which he sees as more significant than the team's results or the absence of goals on the pitch.

Sergio Conceiçao has not brought the benefits that all the supporters were expecting. Milan is in ninth place. This is not a position for a club that has written the history of football. We need to stop and seriously reflect with humility.

In response, Conceicao did not hold back his frustration over Sacchi's recent criticism, noting Sacchi's earlier praise contrasted with his current daily attacks in the media.

Two months ago, he said I was an important coach, now he criticizes me every day. I sent him a message, but he didn’t reply…

#Conceicao contro #Sacchi: “Due mesi fa diceva che ero un allenatore importante, adesso mi massacra tutti i giorni. Gli ho scritto un messaggio, non mi ha risposto…”. #ACMilan pic.twitter.com/Gln8BhudCc

— Nicolò Schira (@NicoSchira) March 7, 2025

In another controversial incident, Conceicao's relationship with the Milan officials has seemingly deteriorated. The manager faced a backlash when his spokesperson claimed he felt unsupported by the club's management and criticized the team's structure.

However, Conceicao publicly denied these statements, affirming the club's support and his regular communication with the directors.

🎙️ O porta-voz de Sérgio Conceição tinha afirmaso que o técnico se sente sozinho e sem apoio da diretoria, criticando a estrutura do Milan e o comprometimento do elenco. Mas o treinador negou tudo, dizendo que o clube está com ele e que mantém contato diário com a diretoria.… pic.twitter.com/u4RfHKVGK8

— Andersinho Marques (@Andersinho_ITA) March 7, 2025

The upcoming weeks will be very crucial for Sergio Conceicao, as he will leave no stone unturned to end his tenure at Milan on a high, bringing Rossoneris close to the qualification zone for the continental competitions.