Hakim Ziyech next? The 10 players to move from Chelsea to AC Milan

Quick Reads
Fikayo Tomori and Olivier Giroud celebrate for AC Milan. San Siro, 17 October 2021.

With the January transfer window getting closer by the day the rumour mill is in full swing. One subject of discussion is the future of Chelsea’s Hakim Ziyech.

It feels strange to say that the Moroccan hasn’t had the best time in west London considering he won the Champions League last season, but he has struggled to carve out a place in Thomas Tuchel’s side.

With limited game time, it has emerged as a possibility that Ziyech will depart, potentially on loan.

One of the most reported destinations is Italian giants AC Milan and if he were to make the jump to the Rossoneri, Ziyech would be travelling along a well-trodden path.

So here are the 10 players who have gone from Stamford Bridge to the Red and Black residents of the San Siro.

Tiemoue Bakayoko

Did you know Bakayoko is still technically a Chelsea player? We certainly didn’t.

It never quite worked out for the Frenchman at Stamford Bridge and he is now on his second stint at Milan on loan from the Blues.

But he’s remembered fondly, in the sense that Chelsea fans seem to use him as a stick to further beat Saul with.

Hernan Crespo

Somehow, the name Hernan Crespo even sounds like a Chelsea player. Along with the fact he arrived from an Italian club (Inter) and that his transfer caused a financial controversy over Chelsea’s accounting probably makes him one of the most Chelsea transfers ever.

He had a solid season for the Blues in 2003-04 but when Jose Mourinho arrived he was shipped off to AC Milan on loan where he scored twice in the 2005 Champions League Final loss to Jerzy Dudek… I mean, Liverpool.

“The cultural differences between an Anglo-Saxon country and Italy was just too big,” he has since said of why his time at Chelsea wasn’t as glorious as it could have been.

If he didn’t like Chelsea, imagine what he’d have thought of Chiselhurst.

READ: Hernan Crespo was far from a Chelsea ‘flop’ – just look at these wonderstrikes

Sam Dalla Bona

Italian native Samuele Dalla Bona arrived in Chelsea as a teenager in 1998, but come 2002 he wanted to return to his home country.

AC Milan facilitated that, but it wasn’t the dream return he had imagined and his career petered out.

“If only I could turn back time, I would have stayed [at Chelsea] forever.” He said years later.

“In Italy, football’s repulsive, particularly everything which goes on around it. The pressure, the mentality – I’m not made out for the Italian culture, and I also paid for this.”

An Italian preferring England? Screw your Euros, we’ve got Dalla Bona.

Michael Essien

Essien was a vital part of Chelsea’s early title-winning teams and signed for Milan when he became surplus to requirements in 2014.

His time at Milan wasn’t particularly memorable apart from when rumours circulated on Twitter that he had Ebola, which somehow convinced the club doctor, during the peak of the epidemic.

It definitely wasn’t funny and Essien went on to help raise awareness on the issue. Good for him.

Olivier Giroud

Giroud is probably one of the suavest footballers in recent memory with a trophy cabinet that would make even the most successful players swoon.

He joined Milan from Chelsea in summer 2021. In west London, he was a crucial squad player but more importantly a wonderful way to mock Arsenal fans. Even he got in on the act.

Jimmy Greaves

One of the finest goalscorers of his generation, Greaves had a brief stint with AC Milan in 1961.

He tried to cancel the deal after changing his mind but couldn’t and had to leave Chelsea and London against his will. That set the tone for his time in Milan, which ended when he kicked out at Sampdoria player who had spat on him in a 2-2 draw.

Despite being unhappy in Milan he still managed to score nine goals in his 14 games, a testament to his incredible ability.

Marco van Ginkel

Van Ginkel was a proper Chelsea loanee, the first of his many being to AC Milan in 2014 where he struggled for game time.

He technically only left Chelsea in 2021, but in truth he has been a PSV player since 2016, even becoming club captain whilst still contracted to the Blues.

Fernando Torres

Torres’ time at Chelsea feels like a fever dream, only surpassed by his weird loan to AC Milan in 2014 where nothing went right and which was then made permanent for some reason.

“I went to Italy to play, to be an important player, and at no point did I feel like it. I was in and out of the team, I played on one day, yes, and on another, no. This is not what I had spoken of from the beginning,” he said after moving.

He never played a single game as a permanent Milan player and was loaned out to boyhood club Atletico Madrid for the entirety of his contract.

Fikayo Tomori

The most recent to make a permanent move to Milan is centre-back Tomori, Milan excercising the buy-option in their loan agreement after he impressed.

They love him over there, although he does need to explain what he was doing here. Trying to bamboozle the opposition with his skills perhaps?

Andriy Shevchenko

In 2006 Shevchenko was the marquee signing of the Abramovich era, joining Chelsea from Milan for just over £26million.

Inflated for today’s market, it still makes him the most expensive Premier League transfer of all time at around £140million.

Yet the Ukrainian didn’t quite click at Chelsea, perhaps due to the pressure the deal put on him. He returned to Milan on loan from Chelsea in 2008-09.

More Chelsea

Fernando Torres: The Chelsea ‘flop’ who still stole fans’ hearts

Remembering when Shevchenko caused Roman and Jose to break up

Giroud recreated his finest Arsenal moment for his finest Chelsea moment

Can you name the Chelsea Xl from John Terry’s last game in 2017?