This page lists the head-to-head record of AC Milan vs Ascoli including biggest victories and defeats between the two sides, and H2H stats in all competitions.
Overall H2H Record - Summary
| Total | Ascoli | AC Milan | Draws |
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| Total Matches | 4 | 0 | 3 | 1 |
| At Cino e Lillo del Duca | 2 | 0 | 2 | 0 |
| At San Siro | 2 | 0 | 1 | 1 |
| Serie A Matches | 4 | 0 | 3 | 1 |
| Total Goals Scored | 11 | 3 | 8 | |
Last 50 Ascoli vs AC Milan Matches
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| 2007 18 April | | Serie A | Ascoli Picchio | 2 - 5 | Milan |
| 2006 20 September | | Serie A | Milan | 1 - 0 | Ascoli Picchio |
| 2006 17 January | | Serie A | Milan | 1 - 0 | Ascoli Picchio |
| 2005 27 August | | Serie A | Ascoli Picchio | 1 - 1 | Milan |
Biggest AC Milan Victory vs Ascoli
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| 2007 18 April | | Serie A | Ascoli Picchio | 2 - 5 | Milan |
Biggest Ascoli Defeat vs AC Milan
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| 2007 18 April | | Serie A | Ascoli Picchio | 2 - 5 | Milan |
Last 5 Ascoli Home Matches
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| 2024 10 November | | Serie C1 - A | Ascoli Picchio | 1 - 1 | Pontedera |
| 2024 30 October | | Serie C1 - A | Ascoli Picchio | 1 - 1 | Citta di Campobasso |
| 2024 19 October | | Serie C1 - A | Ascoli Picchio | 0 - 1 | Perugia |
| 2024 6 October | | Serie C1 - A | Ascoli Picchio | 1 - 2 | Pescara |
| 2024 29 September | | Serie C1 - A | Ascoli Picchio | 0 - 1 | Rimini |
Last 5 AC Milan Home Matches
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| 2024 29 October | | Serie A | Milan | 0 - 2 | Napoli |
| 2024 22 October | | UEFA Champions League | Milan | 3 - 1 | Club Brugge |
| 2024 19 October | | Serie A | Milan | 1 - 0 | Udinese |
| 2024 27 September | | Serie A | Milan | 3 - 0 | Lecce |
| 2024 17 September | | UEFA Champions League | Milan | 1 - 3 | Liverpool |
Last 5 Ascoli Away Matches
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| 2024 15 November | | Serie C1 - A | Vis Pesaro | 1 - 1 | Ascoli Picchio |
| 2024 3 November | | Serie C1 - A | Arezzo | 1 - 1 | Ascoli Picchio |
| 2024 27 October | | Serie C1 - A | Pineto | 1 - 0 | Ascoli Picchio |
| 2024 13 October | | Serie C1 - A | Ternana | 3 - 1 | Ascoli Picchio |
| 2024 26 September | | Serie C1 - A | Athletic Carpi | 2 - 2 | Ascoli Picchio |
Last 5 AC Milan Away Matches
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| 2024 9 November | | Serie A | Cagliari | 3 - 3 | Milan |
| 2024 5 November | | UEFA Champions League | Real Madrid | 1 - 3 | Milan |
| 2024 2 November | | Serie A | Monza | 0 - 1 | Milan |
| 2024 6 October | | Serie A | Fiorentina | 2 - 1 | Milan |
| 2024 1 October | | UEFA Champions League | Bayer Leverkusen | 1 - 0 | Milan |