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 15 March | | Serie A | Milan | 2 - 1 | Como |
| 2025 2 March | | Serie A | Milan | 1 - 2 | Lazio |
| 2025 18 February | | UEFA Champions League | Milan | 1 - 1 | Feyenoord |
| 2025 15 February | | Serie A | Milan | 1 - 0 | Hellas Verona |
| 2025 5 February | | Cup | Milan | 3 - 1 | Roma |
Last 5 Ascoli Home Matches
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| 2025 15 March | | Serie C1 - A | Ascoli Picchio | 1 - 0 | Arezzo |
| 2025 8 March | | Serie C1 - A | Ascoli Picchio | 0 - 1 | Pineto |
| 2025 23 February | | Serie C1 - A | Ascoli Picchio | 0 - 3 | Ternana |
| 2025 31 January | | Serie C1 - A | Ascoli Picchio | 2 - 1 | Athletic Carpi |
| 2025 19 January | | Serie C1 - A | Ascoli Picchio | 2 - 2 | Milan II |
Last 5 AC Milan Away Matches
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| 2025 8 March | | Serie A | Lecce | 2 - 3 | Milan |
| 2025 27 February | | Serie A | Bologna | 2 - 1 | Milan |
| 2025 22 February | | Serie A | Torino | 2 - 1 | Milan |
| 2025 12 February | | UEFA Champions League | Feyenoord | 1 - 0 | Milan |
| 2025 8 February | | Serie A | Empoli | 0 - 2 | Milan |
Last 5 Ascoli Away Matches
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| 2025 22 March | | Serie C1 - A | Pontedera | 1 - 1 | Ascoli Picchio |
| 2025 11 March | | Serie C1 - A | Citta di Campobasso | 2 - 0 | Ascoli Picchio |
| 2025 3 March | | Serie C1 - A | Perugia | 2 - 1 | Ascoli Picchio |
| 2025 17 February | | Serie C1 - A | Pescara | 1 - 2 | Ascoli Picchio |
| 2025 8 February | | Serie C1 - A | Rimini | 2 - 0 | Ascoli Picchio |