The 2025/26 football season is in full swing, and AC Milan is among the contenders to get the champion’s title. The football club is among the favourites, but several decisive matches are yet to determine its destiny. Undoubtedly, each contest can play a critical role in the final result, but some meetings are more important. Discover the five upcoming matchups that will affect Milan this season.
AC Milan vs Fiorentina, 19 October
At first glance, this match is nothing but a routine game for AC Milan: it has a clear home-field advantage and is expected to show its best performance at the stadium. Still, Fiorentina is an ambitious team with Stefano Pioli in charge. The Rossoneri, however, were able to grab the victory 2-1 at the San Siro. Rafael Leao scored a brace while Robin Gosens scored for 'La Viola'.
Before the match, Milan was a favourite on sites not on GamStop, with 1.91 odds against the opponent’s 4.10. Still, the club has already made mistakes in such matchups in the recent past. Allegri's Milan team, however, had good momentum and a strong team on paper and were able to ease past Fiorentina.
Atalanta vs AC Milan, 28 October
In October, Milan had quite the busy schedule, and with six injuries overall, the performances dipped a little. First, there was a draw against Igor Tudor's Juventus. Then yesterday, Milan drew again at Bergamo against Ivan Juric's Atalanta team.
The Rossoneri started well by scoring early in the 4th minute but due to fatigue and lack of choices from the bench because of injuries, beating one of the most elite Italian squads in recent years, was complicated for AC Milan. The odds indicated that both clubs have pretty equal chances of winning, which made the match even more exciting for Serie A followers. In the end, the spoils were shared with a 1-1 draw.
Still, the contest did demonstrate the team’s resilience during matches outside the home, especially considering the number of games that are played in a short period. Many football fans still doubt that Milan will be able to overcome such challenges, and a victory under these circumstances would have proven that critics are absolutely wrong.
AC Milan vs Roma, 2 November
Both clubs strive to reach at least top-four finishes, so the competition promises to be tough. In the past, Milan has obviously beaten the opponent from the Italian capital, as the squad had a higher tempo, better organisation, and chemistry among members. Currently, Roma’s attacking strengths and defensive lines have shown significant improvement.
Keeping up with Italian league football updates is essential this season, as experts predict only a few points may separate these clubs. Milan’s performance on the match day is critical. The two teams are also competing for a future qualification to the UEFA Champions League, so even a slight difference will decide their fate.
AC Milan vs Inter, 23 November
Derby della Madonnina is the most important matchup for AC Milan, as the team will compete with Inter, another renowned city’s team. The event will take place in San Siro, the former home of AC Milan. Currently, the two squads share this stadium, so they will both play in the familiar conditions. AC Milan and Inter have the opportunity to secure top positions throughout the season, which adds excitement to this contest.
So, what’s at stake? Firstly, both teams want to maintain pride and local supremacy. Moreover, each aims to remain in the top 3 and continue their performance during the season with higher scores. Mid-season shifts in football betting trends often reflect changes in form and momentum, making this particular match a key indicator for both fans and bookmakers. In this context, Milan’s win can become even more significant for the team and its supporters in Italy and beyond.
AC Milan vs Juventus, 26 April
It’s still too early to predict 2026 matches, but this game will definitely define Milan’s future. The decisive contest with Juventus will take place in April, during the final rounds of the season. This event will define who will get the title and qualify for the UEFA Champions League, so every score can influence the outcome. That’s why every moment on the pitch will count, with both teams giving everything to secure their place at the top.
The latest meeting of the two contenders was held on 5th October and ended in a draw (0-0). Hence, the stakes are high: this match can potentially become the top-2 battle. It’s still a long time before this matchup, so fans of AC Milan should closely follow the team’s performance and look forward to the best.
The Final Battle Ahead
The 2025/26 football season continues: Milan has already shown significant results, but the most important matches are still ahead. Contests with Atlanta, Inter, Fiorentina, Roma, and Juventus will highlight the team’s positions, so it must focus on consistency and strengthening the attacking force. For fans, the upcoming competitions promise excitement and a bit of stress. If Milan manages to beat its opponents, this will become the beginning of a new era for the club’s championship.
