This page lists the head-to-head record of Portimonense vs Oliveirense including biggest victories and defeats between the two sides, and H2H stats in all competitions.
Overall H2H Record - Summary
| Total | Oliveirense | Portimonense | Draws |
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| Total Matches | 11 | 3 | 5 | 3 |
| At Estadio Carlos Osorio | 6 | 2 | 3 | 1 |
| At Estádio Municipal de Portimão | 5 | 1 | 2 | 2 |
| Division2 Matches | 7 | 2 | 4 | 1 |
| Cup Matches | 1 | 0 | 0 | 1 |
| Segunda Liga Matches | 3 | 1 | 1 | 1 |
| Total Goals Scored | 32 | 13 | 19 | |
Last 50 Oliveirense vs Portimonense Matches
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| 2025 8 November | | Segunda Liga | Portimonense | 1 - 1 | UD Oliveirense |
| 2025 6 April | | Segunda Liga | Portimonense | 2 - 3 | UD Oliveirense |
| 2024 9 November | | Segunda Liga | UD Oliveirense | 0 - 2 | Portimonense |
| 2021 17 October | | Cup | UD Oliveirense | 2 - 2 | Portimonense |
| 2011 28 December | | Division2 | Portimonense | 0 - 1 | UD Oliveirense |
| 2010 8 May | | Division2 | UD Oliveirense | 0 - 1 | Portimonense |
| 2010 10 January | | Division2 | Portimonense | 3 - 1 | UD Oliveirense |
| 2009 11 April | | Division2 | UD Oliveirense | 0 - 0 | Portimonense |
| 2008 23 November | | Division2 | Portimonense | 1 - 0 | UD Oliveirense |
| 2002 23 March | | Division2 | Portimonense | 4 - 1 | UD Oliveirense |
| 2001 3 November | | Division2 | UD Oliveirense | 4 - 3 | Portimonense |
Biggest Oliveirense Victory vs Portimonense
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| 2025 6 April | | Segunda Liga | Portimonense | 2 - 3 | UD Oliveirense |
Biggest Portimonense Victory vs Oliveirense
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| 2002 23 March | | Division2 | Portimonense | 4 - 1 | UD Oliveirense |
Biggest Oliveirense Defeat vs Portimonense
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| 2002 23 March | | Division2 | Portimonense | 4 - 1 | UD Oliveirense |
Biggest Portimonense Defeat vs Oliveirense
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| 2025 6 April | | Segunda Liga | Portimonense | 2 - 3 | UD Oliveirense |
Last 5 Oliveirense Home Matches
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| 2026 25 January | | Segunda Liga | UD Oliveirense | 2 - 1 | Penafiel |
| 2026 11 January | | Segunda Liga | UD Oliveirense | 3 - 4 | Feirense |
| 2025 12 December | | Segunda Liga | UD Oliveirense | 2 - 3 | Chaves |
| 2025 29 November | | Segunda Liga | UD Oliveirense | 2 - 0 | Leixoes |
| 2025 3 November | | Segunda Liga | UD Oliveirense | 0 - 2 | Maritimo |
Last 5 Portimonense Home Matches
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| 2026 25 January | | Segunda Liga | Portimonense | 0 - 1 | Feirense |
| 2026 11 January | | Segunda Liga | Portimonense | 0 - 0 | Felgueiras 1932 |
| 2025 14 December | | Segunda Liga | Portimonense | 1 - 2 | Leixoes |
| 2025 30 November | | Segunda Liga | Portimonense | 0 - 2 | Maritimo |
| 2025 8 November | | Segunda Liga | Portimonense | 1 - 1 | UD Oliveirense |
Last 5 Oliveirense Away Matches
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| 2026 17 January | | Segunda Liga | Farense | 0 - 0 | UD Oliveirense |
| 2026 3 January | | Segunda Liga | Felgueiras 1932 | 1 - 0 | UD Oliveirense |
| 2025 22 December | | Segunda Liga | Lusitania Lourosa | 0 - 1 | UD Oliveirense |
| 2025 6 December | | Segunda Liga | Benfica II | 2 - 0 | UD Oliveirense |
| 2025 8 November | | Segunda Liga | Portimonense | 1 - 1 | UD Oliveirense |
Last 5 Portimonense Away Matches
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| 2026 17 January | | Segunda Liga | Penafiel | 0 - 2 | Portimonense |
| 2026 3 January | | Segunda Liga | Farense | 0 - 1 | Portimonense |
| 2025 20 December | | Segunda Liga | Chaves | 0 - 1 | Portimonense |
| 2025 7 December | | Segunda Liga | Lusitania Lourosa | 3 - 2 | Portimonense |
| 2025 23 November | | Segunda Liga | Porto II | 1 - 0 | Portimonense |