Bologna and Milan are the first two teams to qualify for the Coppa Italia quarterfinals. The rossoblù beat Monza 4-0, while the rossoneri won 6-1 at the Meazza against Sassuolo.

Bologna opened the round of 16. Leading with a great shot from outside by Pobega in the 32nd minute, Italiano's team doubled their lead with a touch under by Orsolini three minutes later. However, the winger was also injured on the occasion and had to leave the pitch. In his place was the young Argentine Domínguez, who scored the third in the 63rd minute before Castro's definitive poker in the 76th minute with a shot from sixteen meters.

In the evening, Milan ran riot, scoring six goals against Sassuolo, four of which in the 23rd minute . Chukwueze broke the deadlock in the 12th minute by tapping in a first shot that hit the post, five minutes later Reijnders doubled the score. There was no opposition and the Rossoneri easily made it 3-0 with Chukwueze (a brace in the 21st minute) and the poker with Rafael Leão (23rd minute). In the second half, Calabria rounded off the result with a right-footed shot from a tight angle in the 56th minute, then Abraham also scored again in the 61st minute (in the middle, Mulattieri scored in the 59th minute).

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