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 22 January | | UEFA Champions League | Milan | 1 - 0 | Girona |
| 2025 11 January | | Serie A | Milan | 1 - 1 | Cagliari |
| 2024 29 December | | Serie A | Milan | 1 - 1 | Roma |
| 2024 15 December | | Serie A | Milan | 0 - 0 | Genoa |
| 2024 11 December | | UEFA Champions League | Milan | 2 - 1 | Crvena Zvezda |
Last 5 Ascoli Home Matches
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| 2025 19 January | | Serie C1 - A | Ascoli Picchio | 2 - 2 | Milan II |
| 2025 12 January | | Serie C1 - A | Ascoli Picchio | 0 - 1 | Virtus Entella |
| 2024 20 December | | Serie C1 - A | Ascoli Picchio | 1 - 1 | Real SPAL |
| 2024 6 December | | Serie C1 - A | Ascoli Picchio | 4 - 1 | Sestri Levante |
| 2024 24 November | | Serie C1 - A | Ascoli Picchio | 1 - 0 | Gubbio |
Last 5 AC Milan Away Matches
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| 2025 18 January | | Serie A | Juventus | 2 - 0 | Milan |
| 2025 14 January | | Serie A | Como | 1 - 2 | Milan |
| 2024 20 December | | Serie A | Hellas Verona | 0 - 1 | Milan |
| 2024 6 December | | Serie A | Atalanta | 2 - 1 | Milan |
| 2024 26 November | | UEFA Champions League | Slovan Bratislava | 2 - 3 | Milan |
Last 5 Ascoli Away Matches
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| 2025 6 January | | Serie C1 - A | Pianese | 1 - 1 | Ascoli Picchio |
| 2024 14 December | | Serie C1 - A | Legnago Salus | 0 - 1 | Ascoli Picchio |
| 2024 1 December | | Serie C1 - A | Torres | 1 - 2 | Ascoli Picchio |
| 2024 15 November | | Serie C1 - A | Vis Pesaro | 1 - 1 | Ascoli Picchio |
| 2024 3 November | | Serie C1 - A | Arezzo | 1 - 1 | Ascoli Picchio |