Chelsea vs Milan 8 August 2026 Prediction

Chelsea and Milan have met regularly in friendlies during the 21st century. They have played five such matches, including one in Moscow. The English side has a clear advantage with four wins, including a 4-1 victory at Stamford Bridge last year. For Milan supporters, the main positive from that game was Luka Modric making his debut for the club.

Poor Results Against Top Opposition

None of the three managers who worked with Chelsea last season, Maresca, Rosenior, or MacFarlane, produced the expected results, so the London club begins a new period under Xabi Alonso. The preseason results have not been encouraging so far. Chelsea’s only win came against Australian side Western Sydney Wanderers, 6-4, while the team lost to Tottenham, 2-1, and Juventus, 1-0, in its two matches against stronger opposition.

Alonso has rotated heavily, giving young and reserve players significant minutes in the second half of each friendly. That has affected the team’s organization. Despite taking an attack-minded approach against opponents of a similar level, including a Tottenham side that went down to 10 men in the 49th minute, Chelsea scored only once across those two matches. Alonso has also acknowledged that his players still need to improve their tempo control and ability to play through pressure.

Chelsea also has several personnel issues. The club’s most expensive summer signing, Morgan Rogers from Aston Villa, remains on vacation after the World Cup, along with Reece James and Enzo Fernandez. Cole Palmer missed the Juventus match with a minor injury, further reducing Chelsea’s attacking options. His availability against Milan is also uncertain.

Milan Adapts to a New System

Milan ended the 2025/26 season poorly and once again failed to qualify for the Champions League. The club replaced Massimiliano Allegri with Ruben Amorim, its third Portuguese manager in two years. Milan has drawn every friendly under its new manager so far. One positive was the 1-1 result against Inter, which extended the Rossoneri’s unbeaten derby run to eight matches.

Amorim is implementing a system based on aggressive high pressing and quick ball movement. The team is still adapting, while the young players and reserves who started both friendlies were unable to provide consistent control. Milan improved in attack after making several substitutions in the second half of the derby, but the changes also left more space in defense.

Milan currently has four players who joined directly from Chelsea: Fikayo Tomori, Christian Pulisic, Ruben Loftus-Cheek, and Christopher Nkunku. All except the injured Pulisic are expected to receive playing time against their former club, with Nkunku likely to be Milan’s main attacking threat. The French forward has scored in three of his last four appearances. Summer signings Mario Gila from Lazio and Goncalo Ramos from Paris Saint-Germain could also feature after already making their Milan debuts.

Chelsea vs Milan Predicted Lineup

Chelsea (4-2-3-1): Sanchez; Palestra, Adarabioyo, Fofana, Hato; Lavia, Caicedo; Neto, Joao Pedro, Gittens; Welbeck

Unavailable: Emegha (injured), James, Gusto, Fernandez, Rogers, Lacroix (not included in the squad), Disasi, Chalobah, Badiashile (club decision), Palmer, Colwill (both doubtful)

Manager: Xabi Alonso

Milan (3-4-2-1): Torriani; Gila, Gabbia, Pavlovic; Saelemaekers, Fofana, Loftus-Cheek, Bartesaghi; Chukwueze, Rafael Leao; Nkunku

Unavailable: Pulisic, Gimenez (both injured), Maignan, Rabiot (not included in the squad)

Manager: Ruben Amorim

Chelsea vs Milan Prediction: Milan Double Chance (X2)

Main prediction: Milan has less squad depth than Chelsea and has yet to win during preseason, but the tactical matchup could suit Amorim’s team. Chelsea has struggled to play through aggressive pressure, particularly against Tottenham. High pressing is now a central part of Milan’s approach. Rafael Leao’s pace and Christopher Nkunku’s movement could also cause problems for Chelsea’s high defensive line. With the favorite still winless against strong preseason opposition, our pick is Milan double chance (X2) at odds of 1.90.

Totals prediction: A high-scoring match is less likely. Both teams opened preseason with games that produced plenty of goals, but neither has combined with a strong opponent to score more than three goals in any subsequent friendly. Our additional pick is under 3.5 goals at odds of 1.72.