This page lists the head-to-head record of Oliveirense vs Portimonense including biggest victories and defeats between the two sides, and H2H stats in all competitions.
Overall H2H Record - Summary
| Total | Portimonense | Oliveirense | Draws |
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| Total Matches | 10 | 5 | 3 | 2 |
| At Estádio Municipal de Portimão | 5 | 2 | 1 | 2 |
| At Estadio Carlos Osorio | 5 | 3 | 2 | 0 |
| Division2 Matches | 7 | 4 | 2 | 1 |
| Cup Matches | 1 | 0 | 0 | 1 |
| Segunda Liga Matches | 2 | 1 | 1 | 0 |
| Total Goals Scored | 30 | 18 | 12 | |
Last 50 Portimonense vs Oliveirense Matches
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| 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 Portimonense Victory vs Oliveirense
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| 2002 23 March | | Division2 | Portimonense | 4 - 1 | UD Oliveirense |
Biggest Oliveirense Victory vs Portimonense
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| 2025 6 April | | Segunda Liga | Portimonense | 2 - 3 | UD Oliveirense |
Biggest Portimonense Defeat vs Oliveirense
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| 2025 6 April | | Segunda Liga | Portimonense | 2 - 3 | UD Oliveirense |
Biggest Oliveirense Defeat vs Portimonense
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| 2002 23 March | | Division2 | Portimonense | 4 - 1 | UD Oliveirense |
Last 5 Portimonense Home Matches
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| 2025 27 April | | Segunda Liga | Portimonense | 2 - 2 | Tondela |
| 2025 18 April | | Segunda Liga | Portimonense | 2 - 0 | Pacos de Ferreira |
| 2025 6 April | | Segunda Liga | Portimonense | 2 - 3 | UD Oliveirense |
| 2025 14 March | | Segunda Liga | Portimonense | 1 - 2 | Feirense |
| 2025 2 March | | Segunda Liga | Portimonense | 2 - 1 | Leixoes |
Last 5 Oliveirense Home Matches
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| 2025 25 April | | Segunda Liga | UD Oliveirense | 2 - 0 | Academico Viseu |
| 2025 13 April | | Segunda Liga | UD Oliveirense | 1 - 1 | Porto II |
| 2025 29 March | | Segunda Liga | UD Oliveirense | 1 - 3 | Tondela |
| 2025 9 March | | Segunda Liga | UD Oliveirense | 0 - 1 | Vizela |
| 2025 16 February | | Segunda Liga | UD Oliveirense | 3 - 2 | Benfica II |
Last 5 Portimonense Away Matches
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| 2025 3 May | | Segunda Liga | Academico Viseu | 2 - 1 | Portimonense |
| 2025 12 April | | Segunda Liga | Chaves | 2 - 0 | Portimonense |
| 2025 29 March | | Segunda Liga | Vizela | 3 - 2 | Portimonense |
| 2025 9 March | | Segunda Liga | Benfica II | 0 - 0 | Portimonense |
| 2025 21 February | | Segunda Liga | Penafiel | 3 - 0 | Portimonense |
Last 5 Oliveirense Away Matches
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| 2025 2 May | | Segunda Liga | Uniao de Leiria | 5 - 0 | UD Oliveirense |
| 2025 20 April | | Segunda Liga | Alverca | 4 - 0 | UD Oliveirense |
| 2025 6 April | | Segunda Liga | Portimonense | 2 - 3 | UD Oliveirense |
| 2025 15 March | | Segunda Liga | Chaves | 4 - 0 | UD Oliveirense |
| 2025 3 March | | Segunda Liga | Pacos de Ferreira | 0 - 1 | UD Oliveirense |