This page lists the head-to-head record of Grosseto vs AC Milan including biggest victories and defeats between the two sides, and H2H stats in all competitions.
Overall H2H Record - Summary
| Total | AC Milan | Grosseto | Draws |
| Total Matches | 0 | 0 | 0 | 0 |
| At San Siro | 0 | 0 | 0 | 0 |
| At Stadio Carlo Zecchini | 0 | 0 | 0 | 0 |
| Total Goals Scored | 0 | 0 | 0 | |
Last 5 AC Milan Home Matches
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| 2026 18 January | | Serie A | Milan | 1 - 0 | Lecce |
| 2026 8 January | | Serie A | Milan | 1 - 1 | Genoa |
| 2025 28 December | | Serie A | Milan | 3 - 0 | Hellas Verona |
| 2025 14 December | | Serie A | Milan | 2 - 2 | Sassuolo |
| 2025 29 November | | Serie A | Milan | 1 - 0 | Lazio |
Last 5 Grosseto Home Matches
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| 2022 14 April | | Serie C1 - A | Grosseto | 0 - 2 | Lucchese |
| 2022 3 April | | Serie C1 - A | Grosseto | 0 - 0 | Robur Siena |
| 2022 19 March | | Serie C1 - A | Grosseto | 1 - 0 | Virtus Entella |
| 2022 15 March | | Serie C1 - A | Grosseto | 0 - 0 | Pontedera |
| 2022 6 March | | Serie C1 - A | Grosseto | 2 - 0 | Imolese |
Last 5 AC Milan Away Matches
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| 2026 25 January | | Serie A | Roma | 1 - 1 | Milan |
| 2026 15 January | | Serie A | Como | 1 - 3 | Milan |
| 2026 11 January | | Serie A | Fiorentina | 1 - 1 | Milan |
| 2026 2 January | | Serie A | Cagliari | 0 - 1 | Milan |
| 2025 8 December | | Serie A | Torino | 2 - 3 | Milan |
Last 5 Grosseto Away Matches
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| 2022 23 April | | Serie C1 - A | Olbia | 3 - 1 | Grosseto |
| 2022 9 April | | Serie C1 - A | Pescara | 2 - 1 | Grosseto |
| 2022 27 March | | Serie C1 - A | Montevarchi Calcio | 1 - 1 | Grosseto |
| 2022 12 March | | Serie C1 - A | Vis Pesaro | 2 - 1 | Grosseto |
| 2022 27 February | | Serie C1 - A | Teramo | 2 - 1 | Grosseto |