This page lists the head-to-head record of Estoril Praia vs Oliveirense including biggest victories and defeats between the two sides, and H2H stats in all competitions.
Overall H2H Record - Summary
| Total | Oliveirense | Estoril Praia | Draws |
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| Total Matches | 13 | 1 | 7 | 5 |
| At Estadio Carlos Osorio | 7 | 1 | 4 | 2 |
| At Antònio Coimbra da Mota | 6 | 0 | 3 | 3 |
| Division2 Matches | 7 | 1 | 2 | 4 |
| Segunda Liga Matches | 6 | 0 | 5 | 1 |
| Total Goals Scored | 21 | 4 | 17 | |
Last 50 Oliveirense vs Estoril Praia Matches
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| 2021 26 March | | Segunda Liga | Estoril | 3 - 0 | UD Oliveirense |
| 2020 8 November | | Segunda Liga | UD Oliveirense | 0 - 1 | Estoril |
| 2020 7 March | | Segunda Liga | UD Oliveirense | 1 - 1 | Estoril |
| 2019 27 October | | Segunda Liga | Estoril | 3 - 0 | UD Oliveirense |
| 2019 19 April | | Segunda Liga | Estoril | 3 - 1 | UD Oliveirense |
| 2018 21 December | | Segunda Liga | UD Oliveirense | 0 - 1 | Estoril |
| 2011 25 September | | Division2 | Estoril | 0 - 0 | UD Oliveirense |
| 2011 19 February | | Division2 | Estoril | 2 - 0 | UD Oliveirense |
| 2010 26 September | | Division2 | UD Oliveirense | 1 - 1 | Estoril |
| 2010 30 January | | Division2 | Estoril | 0 - 1 | UD Oliveirense |
| 2009 23 August | | Division2 | UD Oliveirense | 0 - 0 | Estoril |
| 2009 8 February | | Division2 | UD Oliveirense | 0 - 2 | Estoril |
| 2008 31 August | | Division2 | Estoril | 0 - 0 | UD Oliveirense |
Biggest Oliveirense Victory vs Estoril Praia
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| 2010 30 January | | Division2 | Estoril | 0 - 1 | UD Oliveirense |
Biggest Estoril Praia Victory vs Oliveirense
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| 2021 26 March | | Segunda Liga | Estoril | 3 - 0 | UD Oliveirense |
Biggest Oliveirense Defeat vs Estoril Praia
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| 2021 26 March | | Segunda Liga | Estoril | 3 - 0 | UD Oliveirense |
Biggest Estoril Praia Defeat vs Oliveirense
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| 2010 30 January | | Division2 | Estoril | 0 - 1 | UD Oliveirense |
Last 5 Oliveirense Home Matches
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| 2026 7 February | | Segunda Liga | UD Oliveirense | 3 - 0 | Vizela |
| 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 |
Last 5 Estoril Praia Home Matches
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| 2026 7 February | | Portuguese Liga | Estoril | 2 - 2 | Tondela |
| 2026 24 January | | Portuguese Liga | Estoril | 4 - 2 | Guimaraes |
| 2025 27 December | | Portuguese Liga | Estoril | 4 - 1 | Alverca |
| 2025 19 December | | Portuguese Liga | Estoril | 1 - 0 | Sporting Braga |
| 2025 7 December | | Portuguese Liga | Estoril | 3 - 3 | Moreirense |
Last 5 Oliveirense Away Matches
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| 2026 14 February | | Segunda Liga | Academico Viseu | 4 - 1 | UD Oliveirense |
| 2026 1 February | | Segunda Liga | Sporting CP II | 2 - 0 | UD Oliveirense |
| 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 |
Last 5 Estoril Praia Away Matches
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| 2026 15 February | | Portuguese Liga | AVS | 3 - 0 | Estoril |
| 2026 31 January | | Portuguese Liga | Santa Clara | 2 - 4 | Estoril |
| 2026 19 January | | Portuguese Liga | Estrela P | 0 - 5 | Estoril |
| 2026 3 January | | Portuguese Liga | Benfica | 3 - 1 | Estoril |
| 2025 14 December | | Portuguese Liga | Famalicao | 4 - 0 | Estoril |