This page lists the head-to-head record of Ascoli 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 | Ascoli | Draws |
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| Total Matches | 4 | 3 | 0 | 1 |
| At San Siro | 2 | 1 | 0 | 1 |
| At Cino e Lillo del Duca | 2 | 2 | 0 | 0 |
| Serie A Matches | 4 | 3 | 0 | 1 |
| Total Goals Scored | 11 | 8 | 3 | |
Last 50 AC Milan vs Ascoli 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 AC Milan Home Matches
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| 2025 14 December | | Serie A | Milan | 2 - 2 | Sassuolo |
| 2025 29 November | | Serie A | Milan | 1 - 0 | Lazio |
| 2025 2 November | | Serie A | Milan | 1 - 0 | Roma |
| 2025 24 October | | Serie A | Milan | 2 - 2 | Pisa |
| 2025 19 October | | Serie A | Milan | 2 - 1 | Fiorentina |
Last 5 Ascoli Home Matches
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| 2025 8 December | | Serie C1 - A | Ascoli Picchio | 3 - 0 | Forli' |
| 2025 23 November | | Serie C1 - A | Ascoli Picchio | 0 - 2 | Arezzo |
| 2025 7 November | | Serie C1 - A | Ascoli Picchio | 1 - 1 | Gubbio |
| 2025 26 October | | Serie C1 - A | Ascoli Picchio | 1 - 0 | Sambenedettese |
| 2025 12 October | | Serie C1 - A | Ascoli Picchio | 5 - 0 | Pontedera |
Last 5 AC Milan Away Matches
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| 2025 8 December | | Serie A | Torino | 2 - 3 | Milan |
| 2025 4 December | | Cup | Lazio | 1 - 0 | Milan |
| 2025 23 November | | Serie A | Internazionale | 0 - 1 | Milan |
| 2025 8 November | | Serie A | Parma | 2 - 2 | Milan |
| 2025 28 October | | Serie A | Atalanta | 1 - 1 | Milan |
Last 5 Ascoli Away Matches
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| 2025 14 December | | Serie C1 - A | Nuova Monterosi | 0 - 0 | Ascoli Picchio |
| 2025 1 December | | Serie C1 - A | Vis Pesaro | 1 - 1 | Ascoli Picchio |
| 2025 15 November | | Serie C1 - A | Rimini | 0 - 2 | Ascoli Picchio |
| 2025 2 November | | Serie C1 - A | Ravenna | 1 - 0 | Ascoli Picchio |
| 2025 20 October | | Serie C1 - A | Athletic Carpi | 1 - 1 | Ascoli Picchio |