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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| 2026 12 February | | Serie C1 - A | Ascoli Picchio | 2 - 2 | Torres |
| 2026 30 January | | Serie C1 - A | Ascoli Picchio | 3 - 1 | Livorno |
| 2026 25 January | | Serie C1 - A | Ascoli Picchio | 2 - 1 | Perugia |
| 2026 9 January | | Serie C1 - A | Ascoli Picchio | 1 - 0 | Ternana |
| 2025 21 December | | Serie C1 - A | Ascoli Picchio | 0 - 0 | Citta di Campobasso |
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 Ascoli Away Matches
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| 2026 15 February | | Serie C1 - A | Bra | 1 - 3 | Ascoli Picchio |
| 2026 8 February | | Serie C1 - A | Pineto | 1 - 3 | Ascoli Picchio |
| 2026 17 January | | Serie C1 - A | Juventus II | 1 - 0 | Ascoli Picchio |
| 2026 3 January | | Serie C1 - A | Pianese | 4 - 2 | Ascoli Picchio |
| 2025 14 December | | Serie C1 - A | Nuova Monterosi | 0 - 0 | Ascoli Picchio |
Last 5 AC Milan Away Matches
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| 2026 13 February | | Serie A | Pisa | 1 - 2 | Milan |
| 2026 3 February | | Serie A | Bologna | 0 - 3 | Milan |
| 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 |