This page lists the head-to-head record of Siena 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 | Siena | Draws |
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| Total Matches | 18 | 15 | 1 | 2 |
| At San Siro | 9 | 7 | 1 | 1 |
| At Montepaschi Arena | 9 | 8 | 0 | 1 |
| Serie A Matches | 18 | 15 | 1 | 2 |
| Total Goals Scored | 58 | 42 | 16 | |
Last 50 AC Milan vs Siena Matches
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| 2013 19 May | | Serie A | Robur Siena | 1 - 2 | Milan |
| 2013 6 January | | Serie A | Milan | 2 - 1 | Robur Siena |
| 2012 29 April | | Serie A | Robur Siena | 1 - 4 | Milan |
| 2011 17 December | | Serie A | Milan | 2 - 0 | Robur Siena |
| 2010 17 January | | Serie A | Milan | 4 - 0 | Robur Siena |
| 2009 22 August | | Serie A | Robur Siena | 1 - 2 | Milan |
| 2009 15 March | | Serie A | Robur Siena | 1 - 5 | Milan |
| 2008 29 October | | Serie A | Milan | 2 - 1 | Robur Siena |
| 2008 10 February | | Serie A | Milan | 1 - 0 | Robur Siena |
| 2007 15 September | | Serie A | Robur Siena | 1 - 1 | Milan |
| 2007 17 February | | Serie A | Robur Siena | 3 - 4 | Milan |
| 2006 1 October | | Serie A | Milan | 0 - 0 | Robur Siena |
| 2006 21 January | | Serie A | Robur Siena | 0 - 3 | Milan |
| 2005 9 September | | Serie A | Milan | 3 - 1 | Robur Siena |
| 2005 16 April | | Serie A | Robur Siena | 2 - 1 | Milan |
| 2004 13 November | | Serie A | Milan | 2 - 1 | Robur Siena |
| 2004 16 April | | Serie A | Robur Siena | 1 - 2 | Milan |
| 2004 27 January | | Serie A | Milan | 2 - 1 | Robur Siena |
Biggest AC Milan Victory vs Siena
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| 2010 17 January | | Serie A | Milan | 4 - 0 | Robur Siena |
Biggest Siena Victory vs AC Milan
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| 2005 16 April | | Serie A | Robur Siena | 2 - 1 | Milan |
Biggest AC Milan Defeat vs Siena
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| 2005 16 April | | Serie A | Robur Siena | 2 - 1 | Milan |
Biggest Siena Defeat vs AC Milan
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| 2010 17 January | | Serie A | Milan | 4 - 0 | Robur Siena |
Last 5 AC Milan Home Matches
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| 2025 24 October | | Serie A | Milan | 2 - 2 | Pisa |
| 2025 19 October | | Serie A | Milan | 2 - 1 | Fiorentina |
| 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 |
Last 5 Siena Home Matches
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| 2023 23 April | | Serie C1 - A | Robur Siena | 1 - 2 | Virtus Entella |
| 2023 6 April | | Serie C1 - A | Robur Siena | 2 - 2 | Gubbio |
| 2023 18 March | | Serie C1 - A | Robur Siena | 0 - 0 | Alessandria |
| 2023 11 March | | Serie C1 - A | Robur Siena | 4 - 0 | Vis Pesaro |
| 2023 25 February | | Serie C1 - A | Robur Siena | 1 - 1 | Recanatese |
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 |
Last 5 Siena Away Matches
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| 2023 15 April | | Serie C1 - A | Fiorenzuola | 1 - 1 | Robur Siena |
| 2023 1 April | | Serie C1 - A | Fermana | 3 - 1 | Robur Siena |
| 2023 26 March | | Serie C1 - A | Carrarese | 3 - 0 | Robur Siena |
| 2023 14 March | | Serie C1 - A | Lucchese | 1 - 1 | Robur Siena |
| 2023 5 March | | Serie C1 - A | San Donato Tavarnelle | 1 - 1 | Robur Siena |