This battle between two sides fighting for European qualification began in frenetic fashion, with early openings for both sides.
Milan should have scored inside the opening minute when Santiago Giménez blazed a close-range attempt over the bar after Yunas Musah squared the ball into the Mexican’s path.
Malick Thiaw then nearly turned the ball into his own net after diverting a dangerous Benja Domínguez cross just past the far post, with history very nearly repeating itself after the German’s own goal in a 2-1 defeat to Torino last Saturday.
Sérgio Conceição’s side were having their work cut out to match Bologna’s intensity, as Dan Ndoye shot wide from Lewis Ferguson’s lovely long-range ball, before Mike Maigan was forced into a save to deny Benja Domínguez.
Despite all of the hosts’ pressure, it was Milan who took the lead through Rafael Leão. Giménez brought down Maignan’s long ball forward into Leão’s path, before the Portuguese coolly rounded Łukasz Skorupski and slotted the ball into an empty net.
The Rossoblù would have felt rightly aggrieved to head into half time a goal behind, but Santiago Castro restored parity a mere three minutes into the second half. Ferguson’s free-kick caused mayhem in the Milan defence, as Lorenzo De Silvestri headed the ball onto Giovanni Fabbian, who guided it towards Castro to fire home.
Yunus Musah was one of Milan’s liveliest players and almost engineered a superb individual goal after brilliantly weaving his way in from the right-hand side before being denied by Skorupski.
Meanwhile, Juan Miranda was inches away from scoring a spectacular second Bologna goal when the full-back’s ferocious left-footed strike just cleared the crossbar.
Conceição freshened up his forward line with the introduction of Luka Jović for Giménez, and the Serbian had a chance within seconds of entering the pitch when he headed Youssouf Fofana’s cross straight at Skorupski.
However, shortly after Nicolò Casale’s header cannoned off the post, it was Bologna who scored the decisive second goal. The Stadio Renato Dall'Ara erupted into a cacophony of noise after Dan Ndoye expertly slid in Nicolò Cambiaghi’s sublime ball from the left-hand side in the 82nd minute.
This was a fine night’s work for Vincenzo Italiano’s side, who claimed a seventh win from their previous nine home Serie A fixtures, while a troubled campaign for Milan continues, having now only managed to win one of their previous five games across all competitions and slump down a place into eighth.