Chelsea vs AC Milan Prediction and Betting Tips

Premier League giants Chelsea take on Italian heavyweights AC Milan in a pre-season friendly match at Gelora Bung Karno Stadium in Jakarta, Indonesia, on Saturday. The two teams met in pre-season last year, with Chelsea beating Milan 4-1 at Stamford Bridge.

Chelsea had a disappointing 2025-26 season, ending 10th in the standings with 52 points and missing out on Europe completely.

Xabi Alonso has been appointed as the new coach of the Blues, in the hopes that he can turn their fortunes around and ensure a much better season this time around.

If the pre-season period has been an indication of things to come, however, Chelsea fans will be worried, as the London side beat A-League team Western Sydney Wanderers 6-4 before losing 2-1 to Tottenham and 1-0 to Juventus.

This match against Milan gives the Blues a chance to right the ship with a positive result before their final pre-season friendly against Malaysian club Johor Darul Ta’zim on 9 August.

The Premier League kicks off at the end of the month, with Chelsea launching their league campaign with a visit to Fulham on 24 August.

Meanwhile, AC Milan are coming off a disappointing end to last season, where they went from being Scudetto hopefuls for most of the campaign to losing out on UEFA Champions League football on the final day with a 2-1 upset against Cagliari.

The Rossoneri ended in fifth place on 70 points, one point behind Como, who took the final Champions League spot at the expense of Milan.

Previous coach Max Allegri was fired after that disappointing finale, and Portuguese coach Ruben Amorim was brought in.

Milan’s pre-season tour has featured two draws, with a 2-2 stalemate against Scottish champions Celtic at Celtic Park on 25 July followed by a 1-1 draw against city rivals and reigning Serie A champions Inter Milan on 5 August.

After this match against Chelsea, Milan will take on another English side, Manchester United, in a friendly on 15 August. A week later, the Serie A season will begin, with the Rossoneri set to travel to face Torino in the first matchday on 23 August.

Chelsea vs AC Milan head-to-head stats and key numbers

Chelsea and AC Milan have played four competitive matches in the past, with Chelsea winning twice and two other games ending in draws.
The two teams last played against each other in August 2025, in a pre-season friendly at Stamford Bridge, which Chelsea won 4-1.
Chelsea recorded 14 wins, 14 losses, and 10 draws in the English Premier League last season.
AC Milan have won the UEFA Champions League (and previously, the European Cup) seven times, while Chelsea have won two Champions League titles.

Chelsea vs AC Milan prediction

Both clubs have new coaches at the helm, and they will use this game as an opportunity to keep embedding new tactics and getting their players used to their favored style of play.

AC Milan’s pre-season has produced two draws already, and we expect this one to end all square in Jakarta.

Prediction: Chelsea 1-1 AC Milan