Historical record, recent meetings, scoring profile and performance vs the model's pre-match favorite.
| Date | Match | Result | Winner | Model Projection |
|---|---|---|---|---|
| 2027-03-14 | Scheduled | |||
| 2026-10-11 | Scheduled | |||
| 2026-05-03 | 2–0 | Sassuolo +2 | AC Milan 48% | |
| 2025-12-14 | 2–2 | Draw | AC Milan 69% | |
| 2024-04-14 | 3–3 | Draw | AC Milan 63% | |
| 2023-12-30 | 1–0 | AC Milan +1 | AC Milan 69% | |
| 2023-01-29 | 2–5 | Sassuolo +3 | AC Milan 68% | |
| 2022-08-30 | 0–0 | Draw | AC Milan 48% | |
| 2022-05-22 | 0–3 | AC Milan +3 | AC Milan 47% | |
| 2021-11-28 | 1–3 | Sassuolo +2 | AC Milan 64% | |
| 2021-04-21 | 1–2 | Sassuolo +1 | AC Milan 60% | |
| 2020-12-20 | 1–2 | AC Milan +1 | AC Milan 42% | |
| 2020-07-21 | 1–2 | AC Milan +1 | AC Milan 38% | |
| 2019-12-15 | 0–0 | Draw | AC Milan 56% | |
| 2019-03-02 | 1–0 | AC Milan +1 | AC Milan 65% | |
| 2018-09-30 | 1–4 | AC Milan +3 | AC Milan 37% | |
| 2018-04-08 | 1–1 | Draw | AC Milan 64% | |
| 2017-11-05 | 0–2 | AC Milan +2 | AC Milan 42% | |
| 2017-02-26 | 0–1 | AC Milan +1 | AC Milan 44% | |
| 2016-10-02 | 4–3 | AC Milan +1 | AC Milan 50% | |
| 2016-03-06 | 2–0 | Sassuolo +2 | AC Milan 38% | |
| 2015-10-25 | 2–1 | AC Milan +1 | AC Milan 44% | |
| 2015-05-17 | 3–2 | Sassuolo +1 | AC Milan 37% | |
| 2015-01-06 | 1–2 | Sassuolo +1 | AC Milan 56% | |
| 2014-05-18 | 2–1 | AC Milan +1 | AC Milan 66% | |
| 2014-01-12 | 4–3 | Sassuolo +1 | AC Milan 53% |