This page lists the head-to-head record of AC Milan vs Bologna including biggest victories and defeats between the two sides, and H2H stats in all competitions.
Overall H2H Record - Summary
| Total | Bologna | AC Milan | Draws |
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| Total Matches | 52 | 8 | 33 | 11 |
| At Renato Dall'Ara | 27 | 4 | 17 | 6 |
| At San Siro | 25 | 4 | 16 | 5 |
| Cup Matches | 1 | 1 | 0 | 0 |
| Serie A Matches | 51 | 7 | 33 | 11 |
| Total Goals Scored | 139 | 46 | 93 | |
Last 50 Bologna vs AC Milan Matches
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| 2025 14 September | | Serie A | Milan | 1 - 0 | Bologna |
| 2025 14 May | | Cup | Milan | 0 - 1 | Bologna |
| 2025 9 May | | Serie A | Milan | 3 - 1 | Bologna |
| 2025 27 February | | Serie A | Bologna | 2 - 1 | Milan |
| 2024 27 January | | Serie A | Milan | 2 - 2 | Bologna |
| 2023 21 August | | Serie A | Bologna | 0 - 2 | Milan |
| 2023 15 April | | Serie A | Bologna | 1 - 1 | Milan |
| 2022 27 August | | Serie A | Milan | 2 - 0 | Bologna |
| 2022 4 April | | Serie A | Milan | 0 - 0 | Bologna |
| 2021 23 October | | Serie A | Bologna | 2 - 4 | Milan |
| 2021 30 January | | Serie A | Bologna | 1 - 2 | Milan |
| 2020 21 September | | Serie A | Milan | 2 - 0 | Bologna |
| 2020 18 July | | Serie A | Milan | 5 - 1 | Bologna |
| 2019 8 December | | Serie A | Bologna | 2 - 3 | Milan |
| 2019 6 May | | Serie A | Milan | 2 - 1 | Bologna |
| 2018 18 December | | Serie A | Bologna | 0 - 0 | Milan |
| 2018 29 April | | Serie A | Bologna | 1 - 2 | Milan |
| 2017 10 December | | Serie A | Milan | 2 - 1 | Bologna |
| 2017 21 May | | Serie A | Milan | 3 - 0 | Bologna |
| 2017 8 February | | Serie A | Bologna | 0 - 1 | Milan |
| 2016 7 May | | Serie A | Bologna | 0 - 1 | Milan |
| 2016 6 January | | Serie A | Milan | 0 - 1 | Bologna |
| 2014 14 February | | Serie A | Milan | 1 - 0 | Bologna |
| 2013 25 September | | Serie A | Bologna | 3 - 3 | Milan |
| 2013 20 January | | Serie A | Milan | 2 - 1 | Bologna |
| 2012 1 September | | Serie A | Bologna | 1 - 3 | Milan |
| 2012 22 April | | Serie A | Milan | 1 - 1 | Bologna |
| 2011 11 December | | Serie A | Bologna | 2 - 2 | Milan |
| 2011 1 May | | Serie A | Milan | 1 - 0 | Bologna |
| 2010 12 December | | Serie A | Bologna | 0 - 3 | Milan |
| 2010 7 February | | Serie A | Bologna | 0 - 0 | Milan |
| 2009 20 September | | Serie A | Milan | 1 - 0 | Bologna |
| 2009 25 January | | Serie A | Bologna | 1 - 4 | Milan |
| 2008 31 August | | Serie A | Milan | 1 - 2 | Bologna |
| 2005 29 January | | Serie A | Milan | 0 - 1 | Bologna |
| 2004 18 September | | Serie A | Bologna | 0 - 2 | Milan |
| 2004 31 January | | Serie A | Bologna | 0 - 2 | Milan |
| 2003 12 September | | Serie A | Milan | 2 - 1 | Bologna |
| 2003 16 May | | Serie A | Milan | 3 - 1 | Bologna |
| 2003 11 January | | Serie A | Bologna | 0 - 2 | Milan |
| 2002 9 March | | Serie A | Bologna | 2 - 0 | Milan |
| 2001 27 October | | Serie A | Milan | 0 - 0 | Bologna |
| 2001 16 February | | Serie A | Milan | 3 - 3 | Bologna |
| 2000 14 October | | Serie A | Bologna | 2 - 1 | Milan |
| 2000 11 February | | Serie A | Bologna | 2 - 3 | Milan |
| 1999 24 September | | Serie A | Milan | 4 - 0 | Bologna |
| 1999 23 January | | Serie A | Bologna | 2 - 3 | Milan |
| 1998 11 September | | Serie A | Milan | 3 - 0 | Bologna |
| 1998 18 April | | Serie A | Bologna | 3 - 0 | Milan |
| 1997 20 December | | Serie A | Milan | 0 - 0 | Bologna |
Biggest Bologna Victory vs AC Milan
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| 1998 18 April | | Serie A | Bologna | 3 - 0 | Milan |
Biggest AC Milan Victory vs Bologna
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| 1999 24 September | | Serie A | Milan | 4 - 0 | Bologna |
Biggest Bologna Defeat vs AC Milan
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| 1999 24 September | | Serie A | Milan | 4 - 0 | Bologna |
Biggest AC Milan Defeat vs Bologna
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| 1998 18 April | | Serie A | Bologna | 3 - 0 | Milan |
Last 5 Bologna Home Matches
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| 2026 7 January | | Serie A | Bologna | 0 - 2 | Atalanta |
| 2025 28 December | | Serie A | Bologna | 1 - 1 | Sassuolo |
| 2025 14 December | | Serie A | Bologna | 0 - 1 | Juventus |
| 2025 4 December | | Cup | Bologna | 2 - 1 | Parma |
| 2025 1 December | | Serie A | Bologna | 1 - 3 | Cremonese |
Last 5 AC Milan Home Matches
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| 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 |
| 2025 2 November | | Serie A | Milan | 1 - 0 | Roma |
Last 5 Bologna Away Matches
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| 2026 15 January | | Serie A | Hellas Verona | 2 - 3 | Bologna |
| 2026 10 January | | Serie A | Como | 1 - 1 | Bologna |
| 2026 4 January | | Serie A | Internazionale | 3 - 1 | Bologna |
| 2025 11 December | | UEFA Europa League | Celta Vigo | 1 - 2 | Bologna |
| 2025 7 December | | Serie A | Lazio | 1 - 1 | Bologna |
Last 5 AC Milan Away Matches
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| 2026 15 January | | Serie A | Como | 1 - 3 | Milan |
| 2026 11 January | | Serie A | Fiorentina | 1 - 1 | Milan |
| 2026 2 January | | Serie A | Cagliari | 0 - 1 | Milan |
| 2025 8 December | | Serie A | Torino | 2 - 3 | Milan |
| 2025 4 December | | Cup | Lazio | 1 - 0 | Milan |