| Date | League | Home | Results | Away | HT | HDP | W/L |
|---|---|---|---|---|---|---|---|
| 2026-01-30 01:00 | IW Cup | Fiorentina (W) | 1:0 | AC Milan (W) | 0:0 | 0.75 | Win |
| 2026-01-21 01:00 | IW Cup | AC Milan (W) | 1:1 | Fiorentina (W) | 0:1 | 0.25 | Win |
| 2026-02-15 22:00 | IW Cup | AC Milan (W) | 0:0 | Fiorentina (W) | 0:0 | ||
| 2025-10-19 21:00 | IW Cup | Fiorentina (W) | 0:0 | AC Milan (W) | 0:0 | ||
| 2025-04-12 20:00 | IW Cup | AC Milan (W) | 0:0 | Fiorentina (W) | 0:0 | ||
| 2025-03-03 01:00 | IW Cup | Fiorentina (W) | 0:0 | AC Milan (W) | 0:0 | 0.25 | Lose |
| 2025-01-29 03:45 | IW Cup | Fiorentina (W) | 2:0 | AC Milan (W) | 1:0 | 0.5 | Win |
| 2025-01-17 01:00 | IW Cup | AC Milan (W) | 1:1 | Fiorentina (W) | 0:1 | 0 | Draw |
| 2024-11-24 19:30 | IW Cup | Fiorentina (W) | 2:2 | AC Milan (W) | 2:0 | 0.75 | Lose |
| 2024-09-15 00:00 | IW Cup | AC Milan (W) | 0:0 | Fiorentina (W) | 0:0 | ||
| 2024-02-03 22:00 | IW Cup | AC Milan (W) | 2:2 | Fiorentina (W) | 2:1 | ||
| 2023-11-04 22:00 | IW Cup | Fiorentina (W) | 0:0 | AC Milan (W) | 0:0 | ||
| 2023-05-07 20:30 | IW Cup | Fiorentina (W) | 1:1 | AC Milan (W) | 1:0 | ||
| 2023-03-26 20:30 | IW Cup | AC Milan (W) | 3:3 | Fiorentina (W) | 2:0 | 0.75 | Win |
| 2023-02-08 19:30 | IW Cup | AC Milan (W) | 1:1 | Fiorentina (W) | 1:1 | 0.75 | Win |
| 2023-01-25 21:30 | IW Cup | Fiorentina (W) | 0:1 | AC Milan (W) | 0:0 | -0.5 | Lose |
| 2022-11-26 21:30 | IW Cup | Fiorentina (W) | 1:6 | AC Milan (W) | 0:4 | ||
| 2022-08-28 23:30 | IW Cup | AC Milan (W) | 1:3 | Fiorentina (W) | 0:3 | 1 | Win |
| 2022-03-27 18:30 | IW Cup | AC Milan (W) | 2:0 | Fiorentina (W) | 1:0 | 1 | Lose |
| 2021-10-31 19:30 | IW Cup | Fiorentina (W) | 0:1 | AC Milan (W) | 0:1 | -0.5 | Lose |
| 2021-01-07 01:00 | IW Cup | Fiorentina (W) | 2:1 | AC Milan (W) | 0:1 | -1 | Win |
| 2021-05-09 18:30 | IW Cup | AC Milan (W) | 1:3 | Fiorentina (W) | 0:1 | ||
| 2020-12-05 19:30 | IW Cup | Fiorentina (W) | 0:1 | AC Milan (W) | 0:1 | 0 | Lose |
| Date | League | Home | Results | Away | HT | HDP | W/L |
|---|---|---|---|---|---|---|---|
| 2025-12-21 21:30 | IW Cup | Bologna W | 1:1 | Fiorentina (W) | 0:1 | ||
| 2025-09-14 18:30 | IW Cup | Fiorentina (W) | 2:1 | Genoa (W) | 1:0 | 1.25 | Win |
| 2025-09-07 00:00 | IW Cup | Inter Milan (W) | 3:1 | Fiorentina (W) | 2:0 | 0.25 | Lose |
| 2026-02-08 22:00 | IW Cup | Inter Milan (W) | 0:0 | Fiorentina (W) | 0:0 | ||
| 2026-02-03 01:00 | IW Cup | Fiorentina (W) | 0:0 | Napoli (W) | 0:0 | ||
| 2026-01-24 22:00 | IW Cup | Lazio (W) | 3:0 | Fiorentina (W) | 2:0 | ||
| 2026-01-17 22:00 | IW Cup | Fiorentina (W) | 1:1 | Genoa (W) | 1:0 | 1.75 | Win |
| 2025-12-13 19:30 | IW Cup | Como 2000 (W) | 1:3 | Fiorentina (W) | 1:1 | -0.75 | Win |
| 2025-12-07 22:00 | IW Cup | Fiorentina (W) | 1:0 | Ternana W | 1:0 | 1.5 | Win |
| 2025-11-23 22:00 | IW Cup | Juventus (W) | 1:0 | Fiorentina (W) | 0:0 | ||
| 2025-11-15 22:00 | IW Cup | Parma s (W) | 1:1 | Fiorentina (W) | 0:0 | -1 | Lose |
| 2025-11-08 03:00 | IW Cup | Fiorentina (W) | 5:2 | Roma CF (W) | 1:0 | ||
| 2025-11-02 22:00 | IW Cup | Sassuolo (W) | 0:0 | Fiorentina (W) | 0:0 | ||
| 2025-10-12 21:00 | IW Cup | Fiorentina (W) | 0:0 | Inter Milan (W) | 0:0 | ||
| 2025-10-04 21:00 | IW Cup | Napoli (W) | 0:0 | Fiorentina (W) | 0:0 | ||
| 2025-03-07 01:00 | IW Cup | Juventus (W) | 1:0 | Fiorentina (W) | 1:0 | 1.25 | Win |
| 2025-05-10 21:00 | IW Cup | Fiorentina (W) | 0:0 | Roma CF (W) | 0:0 | ||
| 2025-05-03 18:30 | IW Cup | Inter Milan (W) | 1:3 | Fiorentina (W) | 1:2 | 0.75 | Win |
| 2025-04-25 18:30 | IW Cup | Fiorentina (W) | 3:1 | Juventus (W) | 2:0 | ||
| 2025-03-29 21:00 | IW Cup | Roma CF (W) | 0:0 | Fiorentina (W) | 0:0 | ||
| 2025-03-23 19:30 | IW Cup | Fiorentina (W) | 1:0 | Inter Milan (W) | 0:0 | 0 | Lose |
| 2025-03-15 22:00 | IW Cup | Juventus (W) | 0:2 | Fiorentina (W) | 0:1 | 1.25 | Win |
| 2025-02-16 22:00 | IW Cup | Fiorentina (W) | 2:3 | Juventus (W) | 2:2 | ||
| 2025-01-06 22:30 | IW Cup | Roma CF (W) | 3:1 | Fiorentina (W) | 1:0 | 1 | Lose |
| 2024-11-06 21:30 | IW Cup | Arezzo W | 0:1 | Fiorentina (W) | 0:1 | -3.25 | Lose |
| 2024-09-26 00:30 | IW Cup | VfL Wolfsburg (W) | 5:0 | Fiorentina (W) | 2:0 | 2 | Lose |
| 2024-09-19 02:00 | IW Cup | Fiorentina (W) | 0:7 | VfL Wolfsburg (W) | 0:4 | -1 | Win |
| 2024-09-07 22:00 | IW Cup | Fiorentina (W) | 0:0 | Ajax (W) | 0:0 | ||
| 2024-09-05 00:00 | IW Cup | Brondby IF (W) | 0:1 | Fiorentina (W) | 0:1 | -1.25 | Lose |
| 2024-08-23 23:00 | IW Cup | Como 2000 (W) | 1:4 | Fiorentina (W) | 1:1 | -1 | Win |
| Date | League | Home | Results | Away | HT | HDP | W/L |
|---|---|---|---|---|---|---|---|
| 2025-12-21 21:30 | IW Cup | Genoa (W) | 2:3 | AC Milan (W) | 0:2 | ||
| 2025-09-14 21:00 | IW Cup | AC Milan (W) | 0:0 | Ternana W | 0:0 | ||
| 2025-09-06 21:00 | IW Cup | Roma CF (W) | 1:0 | AC Milan (W) | 0:0 | 1.5 | Win |
| 2025-08-30 20:00 | IW Cup | Chelsea FC (W) | 4:1 | AC Milan (W) | 2:1 | 2.5 | Lose |
| 2025-08-25 02:30 | IW Cup | AC Milan (W) | 0:2 | Sassuolo (W) | 0:0 | 0.75 | Win |
| 2026-02-08 22:00 | IW Cup | Roma CF (W) | 0:0 | AC Milan (W) | 0:0 | ||
| 2026-02-01 19:30 | IW Cup | AC Milan (W) | 0:0 | Genoa (W) | 0:0 | 1.25 | Win |
| 2026-01-25 19:30 | IW Cup | AC Milan (W) | 3:0 | Ternana W | 1:0 | 1.25 | Lose |
| 2026-01-17 19:30 | IW Cup | Parma s (W) | 0:0 | AC Milan (W) | 0:0 | -0.5 | Lose |
| 2025-12-13 22:00 | IW Cup | AC Milan (W) | 1:5 | Inter Milan (W) | 1:1 | -0.5 | Win |
| 2025-12-06 19:30 | IW Cup | Napoli (W) | 0:2 | AC Milan (W) | 0:0 | -0.5 | Win |
| 2025-11-23 22:30 | IW Cup | AC Milan (W) | 2:2 | Sassuolo (W) | 0:0 | 0.5 | Win |
| 2025-11-16 01:00 | IW Cup | Como 2000 (W) | 1:0 | AC Milan (W) | 0:0 | -0.25 | Lose |
| 2025-11-08 21:00 | IW Cup | AC Milan (W) | 2:1 | Juventus (W) | 1:1 | -0.5 | Lose |
| 2025-11-01 22:00 | IW Cup | AC Milan (W) | 0:0 | Lazio (W) | 0:0 | ||
| 2025-10-12 18:30 | IW Cup | AC Milan (W) | 1:2 | Roma CF (W) | 0:0 | -0.75 | Win |
| 2025-10-05 21:00 | IW Cup | Genoa (W) | 0:0 | AC Milan (W) | 0:0 | ||
| 2025-05-04 18:30 | IW Cup | Roma CF (W) | 3:3 | AC Milan (W) | 2:0 | 1.25 | Win |
| 2025-04-25 22:00 | IW Cup | AC Milan (W) | 1:4 | Inter Milan (W) | 1:1 | -0.25 | Win |
| 2025-04-18 23:30 | IW Cup | Juventus (W) | 2:0 | AC Milan (W) | 1:0 | 1.25 | Lose |
| 2025-03-22 21:00 | IW Cup | AC Milan (W) | 0:0 | Roma CF (W) | 0:0 | ||
| 2025-03-16 20:30 | IW Cup | Inter Milan (W) | 3:3 | AC Milan (W) | 2:1 | 0.75 | Win |
| 2025-03-08 21:00 | IW Cup | AC Milan (W) | 0:0 | Juventus (W) | 0:0 | ||
| 2024-11-06 21:30 | IW Cup | Freedom (ITA) (W) | 0:2 | AC Milan (W) | 0:0 | ||
| 2024-08-24 02:00 | IW Cup | Barcelona (W) | 2:0 | AC Milan (W) | 1:0 | 3.5 | Win |
| 2025-02-09 22:00 | IW Cup | AC Milan (W) | 0:6 | Juventus (W) | 0:4 | -0.5 | Win |
| 2025-02-01 22:00 | IW Cup | Sassuolo (W) | 0:0 | AC Milan (W) | 0:0 | ||
| 2025-01-25 22:00 | IW Cup | AC Milan (W) | 3:2 | Roma CF (W) | 1:2 | ||
| 2025-01-19 19:30 | IW Cup | Sampdoria (W) | 2:2 | AC Milan (W) | 0:0 | -1.5 | Lose |
| 2025-01-12 19:30 | IW Cup | AC Milan (W) | 6:0 | Napoli (W) | 5:0 | 1.75 | Lose |
