Christian Pulisic’s old flames vs. new home: Milan vs Chelsea set for friendly showdown – When and where will it take place?

In a storyline that brings together nostalgia, ambition, and a transcontinental rivalry, Milan and Chelsea have officially confirmed a high-profile summer friendly.

In a storyline that brings together nostalgia, ambition, and a transcontinental rivalry, Milan and Chelsea have officially confirmed a high-profile summer friendly, rekindling memories of past European duels and reigniting interest in the ever-growing soccer bond between these two historic clubs.

This encounter carries added weight not just because of the badge-to-badge battle between two of Europe’s biggest names, but because it revolves around a player who has worn both shirts with pride: Christian Pulisic.

Chelsea’s announcement of the friendly came as part of the “VisitMalta Cup”— a two-day event that sees the Blues welcome Bayer Leverkusen on Friday, followed by Milan on Sunday. “Both games will be played at Stamford Bridge, giving fans a chance to catch the team in action before the Premier League kicks off the following weekend,” Chelsea stated via their official website.

Though billed as a pre-season warm-up, this fixture comes with emotional and symbolic stakes. For Pulisic, it marks a return to the stadium where he spent four rollercoaster years, from his move from Borussia Dortmund in 2019 to his eventual departure in 2023.

During his time in the Premier League, Pulisic experienced both Champions League glory and prolonged injury struggles. While his potential was never fully realized in West London, he left with the respect of fans and teammates alike. Now, at Milan, the 26-year-old has been resurgent, earning a place in the Serie A Team of the Season for 2023-24 and becoming a crucial figure in the Rossoneri attack.

When and where will it take place?

The much-anticipated clash will take place on Sunday, August 10, at Stamford Bridge. The match follows the Rossoneri’s friendly against Leeds United in Dublin the day before, part of a packed pre-season itinerary aimed at sharpening the squad for a vital Serie A campaign.

Milan’s official website confirmed: “This consecutive weekend of top-level opposition will give coach Allegri’s squad an excellent test before the start of the 2025/26 season.”

Packed summer

This London showdown with Chelsea is one of five friendlies Milan will contest during their 2025 pre-season. Prior to the English double-header, the Italian giants will embark on an Asia-Pacific tour, including games against Arsenal in Singapore (July 23), Liverpool in Hong Kong (July 26), and Perth Glory in Australia (July 31).

The clash with the Blues is particularly significant considering their last meetings during the 2022-23 UEFA Champions League group stage, where the Italians lost twice — a 3-0 defeat at Stamford Bridge followed by a 2-0 loss at San Siro. This match, while a friendly, offers a chance for symbolic redemption.

Beyond the matchday headlines, the two sides have developed a curious transfer relationship in recent years. Several players have moved between the two clubs, particularly from Stamford Bridge to the San Siro. Fikayo Tomori, Ruben Loftus-Cheek, Olivier Giroud, and Christian Pulisic are just a few examples of players who have rejuvenated their careers in Italy after stalling in London.