Bologna broke the deadlock with a goal from Joshua Zirkzee in the 29th minute before Ruben Loftus-Cheek equalised just before the break and added his second goal seven minutes from time.
Olivier Giroud and Theo Hernandez failed to score penalties for Milan in each half. Giroud missed from the spot after Lewis Ferguson fouled Simon Kjaer and Hernandez hit the post following Sam Beukama's foul on Rafael Leao.
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