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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| 2025 4 October | | Serie C1 - A | Ascoli Picchio | 4 - 1 | Bra |
| 2025 23 September | | Serie C1 - A | Ascoli Picchio | 3 - 0 | Pineto |
| 2025 6 September | | Serie C1 - A | Ascoli Picchio | 0 - 0 | Juventus II |
| 2025 23 August | | Serie C1 - A | Ascoli Picchio | 0 - 0 | Pianese |
| 2025 27 April | | Serie C1 - A | Ascoli Picchio | 1 - 2 | Legnago Salus |
Last 5 AC Milan Home Matches
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| 2025 28 September | | Serie A | Milan | 2 - 1 | Napoli |
| 2025 23 September | | Cup | Milan | 3 - 0 | Lecce |
| 2025 14 September | | Serie A | Milan | 1 - 0 | Bologna |
| 2025 23 August | | Serie A | Milan | 1 - 2 | Cremonese |
| 2025 17 August | | Cup | Milan | 2 - 0 | Bari 1908 |
Last 5 Ascoli Away Matches
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| 2025 27 September | | Serie C1 - A | Torres | 0 - 1 | Ascoli Picchio |
| 2025 20 September | | Serie C1 - A | Livorno | 0 - 3 | Ascoli Picchio |
| 2025 14 September | | Serie C1 - A | Perugia | 0 - 2 | Ascoli Picchio |
| 2025 31 August | | Serie C1 - A | Ternana | 0 - 2 | Ascoli Picchio |
| 2025 23 April | | Serie C1 - A | Sestri Levante | 0 - 0 | Ascoli Picchio |
Last 5 AC Milan Away Matches
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| 2025 5 October | | Serie A | Juventus | 0 - 0 | Milan |
| 2025 20 September | | Serie A | Udinese | 0 - 3 | Milan |
| 2025 29 August | | Serie A | Lecce | 0 - 2 | Milan |
| 2025 18 May | | Serie A | Roma | 3 - 1 | Milan |
| 2025 5 May | | Serie A | Genoa | 1 - 2 | Milan |