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| Date | Match | Score |
|---|---|---|
| 31.10.2025 | FC OSS - Helmond Sport | 0 : 3 |
| 02.02.2025 | FC OSS - Helmond Sport | 1 : 1 |
| 16.09.2024 | Helmond Sport - FC OSS | 1 : 0 |
| 15.03.2024 | FC OSS - Helmond Sport | 1 : 0 |
| 15.09.2023 | Helmond Sport - FC OSS | 1 : 1 |
| 31.03.2023 | FC OSS - Helmond Sport | 2 : 2 |
| 30.09.2022 | Helmond Sport - FC OSS | 1 : 2 |
| 21.01.2022 | Helmond Sport - FC OSS | 1 : 3 |
| 12.11.2021 | FC OSS - Helmond Sport | 0 : 0 |
| 07.05.2021 | Helmond Sport - FC OSS | 1 : 1 |
| Date | Match | Score | Res |
|---|---|---|---|
| 11.09.2026 | Helmond Sport - Jong PSV U21 | 3 - 1 | W |
| 04.09.2026 | Helmond Sport - VVV Venlo | 4 - 2 | W |
| 28.08.2026 | Jong Ajax - Helmond Sport | 3 - 2 | L |
| 21.08.2026 | Helmond Sport - Waalwijk | 1 - 1 | D |
| 14.08.2026 | Roda - Helmond Sport | 2 - 1 | L |
| Date | Match | Score | Res |
|---|---|---|---|
| 11.09.2026 | VVV Venlo - FC OSS | 3 - 1 | L |
| 04.09.2026 | Vitesse - FC OSS | 2 - 1 | L |
| 28.08.2026 | FC OSS - Jong Utrecht | 2 - 1 | W |
| 24.08.2026 | Jong PSV U21 - FC OSS | 1 - 0 | L |
| 15.08.2026 | FC Volendam - FC OSS | 3 - 0 | L |