Matches between Chelsea and AC Milan have long captured the imagination of football fans around the globe, transcending club rivalries to engage the imaginations of millions worldwide. These European powerhouses boast a rich history of facing off on major stages and producing memorable encounters and iconic moments. In this article, we explore the Chelsea F.C. vs A.C. Milan timeline, exploring key moments, memorable encounters and the progression of this legendary rivalry.

Head-to-Head Record

AC Milan and Chelsea have met a number of times since 1966. The Blues have won 3, drawn 3 and lost 1 in the history of competitive matchups. Find the full head-to-head record below:

Date Fixture Final Scoreline Result Competition
February 9, 1966 AC Milan v Chelsea 2-1 L Fairs Cup
February 16, 1966 Chelsea v AC Milan 2-1 W Fairs Cup
March 2, 1966 AC Milan v Chelsea 1-1 D Fairs Cup
September 15, 1999 Chelsea v AC Milan 0-0 D Champions League
October 26, 1999 AC Milan v Chelsea 1-1 D Champions League
October 5, 2022 Chelsea v AC Milan 3-0 W Champions League
October 11, 2022 AC Milan v Chelsea 0-2 W Champions League

1960s: Early Showdowns and European Glory

Chelsea F.C. and A.C. Milan’s rivalry first blossomed during the 1960s. They first met during the 1965/1966 European Cup Winners’ Cup (Fairs Cup) semi-finals, where Milan emerged victorious to advance all the way to the final while the Blues gained valuable experience from this contest.

1990s: Champions League Stalemates

On September 29, 1999 at Stamford Bridge, Chelsea FC and AC Milan met for their inaugural meeting. An electric atmosphere was present as fans eagerly anticipated the encounter between these formidable sides. Both displayed their respective defensive prowess, which resulted in a tight match which ultimately resulted in a goalless draw.

Although neither side were able to score, the match provided an exciting display of tactical battles and individual brilliance. Gianfranco Zola dazzled with his creativity and skill, while Franco Baresi led AC Milan’s defence expertly with his experience and leadership. Both backlines held firm against one another so neither team managed a breakthrough, leaving this tie poised perfectly going into its return leg.

The rematch took place on November 3, 1999, at the iconic San Siro stadium in Milan. The game proved to be another tightly contested affair, with both teams showcasing their defensive solidity and tactical discipline.

2020s: Blues Dominance to Round out Chelsea F.C. vs A.C. Milan Timeline

Chelsea cruised to a 3-0 home victory over AC Milan in their UEFA Champions League group stage match in 2022. The Blues were in control from the start and took the lead in the 10th minute through Romelu Lukaku. Lukaku doubled Chelsea’s lead in the 25th minute, and Hakim Ziyech added a third goal in the 55th minute. AC Milan never really threatened to get back into the match, and the Blues ran out comfortable winners.

Chelsea followed up with a 2-0 away win just six days later, as as Jorginho and Aubameyang found the target against Milan’s ten men.


The timeline of matches between Chelsea F.C. and A.C. Milan is evidence of their longstanding rivalry and its impactful competitions, such as European clashes or iconic players gracing the field – these encounters have delighted fans across generations.

As both clubs continue to compete at an elite level, the Chelsea FC vs AC Milan rivalry will remain enthralling to fans around the globe. New chapters await to be written as this timeless football tale continues its epic tale.