Chelsea vs AC Milan: Blues’ Old Boys Aim to Dent Their Knockout Hopes

Fikayo Tomori and Olivier Giroud in their Chelsea days

Chelsea host AC Milan in what is set to be an exciting UEFA Champions League Group E encounter on Wednesday night. Among the Milan squad are two Blues’ old boys, who will be aiming to put a severe dent in their hopes to progress to the knockout rounds.

Chelsea currently sit bottom of Group E, having lost to Dinamo Zagreb in what proved to be Thomas Tuchel’s last game in charge of the Blues, and a home draw against Austrian side RB Salzburg. However, Chelsea come into the fixture off the back of new manager Graham Potter’s first win charge. The former Brighton boss will be desperate for his side to build on the weekend’s result.

Chelsea striker Pierre – Emerick Aubameyang celebrating against Crystal Palace
Chelsea striker Pierre – Emerick Aubameyang celebrating against Crystal Palace

Serie A champions AC Milan sit top of the group, having beaten Zagreb at the San Siro and also picking up a draw against RB Salzburg. The Rossoneri are currently 5th in the Italian top-flight, 3 points off league-leaders Napoli as Serie A proves to be as exciting as ever. Milan picked up an away win against Empoli on Saturday, but will be looking for a victory in Wednesday’s match to build momentum ahead of a clash with Juventus at the San Siro this weekend.

Among AC Milan’s squad are two former Chelsea players in Fikayo Tomori and Olivier Giroud.

The former is a product of the famous Cobham, Chelsea’s academy. Tomori left to join Milan in January 2021 on an initial loan with an option to buy. Within three months of his arrival, many Serie A fans began to put his name in the conversation for the league’s best defender. The England International was a rock at the back for the Rossoneri, even drawing praise from Paolo Maldini, who is a current Milan director.

Milan had zero qualms about exercising the option to buy clause in his loan, making the deal permanent for a bargain £25million. Tomori went on to play an absolutely influential role in Milan’s first Serie A title win since 2011 last campaign, as he was part of the best defence in the league.

Given that Chelsea have splashed the cash this past summer on Wesley Fofana and Kalidou Koulibaly, Tomori will be eager to showcase his ability at Stamford Bridge to give Chelsea a sense of what they could’ve had.

AC Milan defender FIkayo Tomori
AC Milan defender FIkayo Tomori

Another ex-Chelsea player in the Milan ranks is Olivier Giroud, who spent nearly four seasons with the Blues after signing from London rivals Arsenal. The French International won three pieces of silverware during his time in West London, namely the FA Cup, the Europa League and the Champions League in 2021.

The striker spoke about his excitement to play his former club and how much he enjoyed his time in London.

“I think it’ll be a special game for the team because it’s a great Champions League match-up. It’s also personally for me, as I spent nine years in London playing for Arsenal and Chelsea, so I expect it to be a great game,” said Giroud on the Milan Channel via Football Italia.

“It’s always a pleasure when the people you met while playing for your former clubs have so much respect for you, also because I want to be seen not only as a good player on the pitch, but also a good person off it. I have many friends in London.”

Giroud also spoke about his Milan side’s chances in this year’s competition.

“I have a lot of hope for our Champions League journey this season. I am very proud of this squad and I think we can do well with this group of players in the Champions League. This match can also give the team great confidence if we win, to boost us for the next games.”

Both players will be looking to hand Graham Potter his first loss as Chelsea boss, and sink the Blues’ chances of progressing further in the tournament. After Wednesday’s fixture against the Italian champions, Chelsea play Wolves at Stamford Bridge, who also recently sacked their manager.

AC Milan striker Olivier Giroud
AC Milan striker Olivier Giroud


Chelsea 1 – 1 AC Milan

Milan come into the game arguably as favourites, albeit marginally. However, given how important the game is to Chelsea’s hopes of advancing to the next round, we think the Blues will give a right go at it, in what is Potter’s first real big European night.

The Italian giants may come away with a result, given the drive bound to be shown by the old Chelsea players on their return. Rafael Leao will also want to stamp his authority on the game as speculation continues to mount over his future as Europe’s elite queue up for the Portuguese star.