AC Milan vs Bologna Prediction & Betting Tips (14 September)

Very disappointing last year, Milan AC ended up a little brilliant 8th place in Serie A. The Lombard training is therefore deprived of the European Cup this season. The leaders made the decision to entrust the reins of the team to Max Allegri. The technician thus finds a bench he occupied from 2010 to 2014. Eager to replay the leading roles in this exercise 2025/2026, the Rossoneri did not reassure the observers during the 1st day. Indeed, despite the support of the tifosi, they lost against the promoted Cremonese 1-2. Just before the international break, AC Milan reacted by winning at Lecce 0-2.

 Now considered as a serious pretender to European strapontines, Bologna finished 9th in the series last year with 1 point behind his opponent of the day. Nevertheless, the classification is in trompe-l'oeil since the club finished the championship in a free wheel due to its career and its victory in the Italian Cup. This title allowed him to qualify for the Europa League. This season, the Rossoblu feeds legitimate ambitions. Beaten on the field of Roma to start 0-1, they then reacted by dominating Como at home 1-0. 

Tactically, Milan’s midfield overhaul could be the deciding factor. Allegri’s new-look engine room—featuring Modric, Loftus-Cheek, and Fofana—has the potential to dominate possession and dictate tempo. Bologna’s compact shape and counter-attacking style will test Milan’s defensive transitions, especially with Estupiñán and Pavlović still adjusting to Serie A’s pace. Expect Milan to control the early phases, but Bologna’s resilience and Rowe’s potential cameo could shift momentum late in the game. The San Siro crowd will be eager to see signs of cohesion from their revamped squad, and Allegri knows that anything less than three points will raise eyebrows.

Prediction-wise, this one leans toward a narrow Milan victory. Bologna’s defensive structure will frustrate the hosts, but Milan’s individual quality—particularly from Nkunku and Pulisic—should be enough to edge it. A 2–1 scoreline feels fitting: Milan to strike early, Bologna to respond with grit, and a late winner to seal the Rossoneri’s first home triumph of the season. It won’t be flawless, but it will be a step forward for a team still finding its rhythm amid sweeping change.

• Summary: Milan is going head to head with Bologna starting on 14 Sept 2025 at 18:45 UTC at San Siro/Giuseppe Meazza stadium, Milan city, Italy. The match is a part of the Serie A .
• Referee: Matteo Marcenaro