| 1. Ronde | 26.08.2023 | AC Monza [A-jun] | - | AC Milan [A-jun] | 1:3 | ||||
| 2. Ronde | 02.09.2023 | AC Milan [A-jun] | - | Bologna FC [A-jun] | 4:1 |  |
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| 3. Ronde | 16.09.2023 | Sassuolo Calcio [A-jun] | - | AC Milan [A-jun] | 0:2 | ||||
| 4. Ronde | 23.09.2023 | AC Milan [A-jun] | - | Juventus [A-jun] | 3:0 | ||||
| 5. Ronde | 30.09.2023 | ACF Fiorentina [A-jun] | - | AC Milan [A-jun] | 1:1 | ||||
| 6. Ronde | 08.10.2023 | AC Milan [A-jun] | - | Atalanta [A-jun] | 3:1 | ||||
| 7. Ronde | 21.10.2023 | AS Roma [A-jun] | - | AC Milan [A-jun] | 0:0 | ||||
| 9. Ronde | 04.11.2023 | Empoli FC [A-jun] | - | AC Milan [A-jun] | 2:1 |
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