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| Date | Match | Score |
|---|---|---|
| 06.02.2026 | Helmond Sport - Den Bosch | 2 : 0 |
| 21.10.2025 | Den Bosch - Helmond Sport | 1 : 0 |
| 02.05.2025 | Den Bosch - Helmond Sport | 1 : 0 |
| 06.12.2024 | Helmond Sport - Den Bosch | 0 : 0 |
| 02.02.2024 | Den Bosch - Helmond Sport | 0 : 0 |
| 18.08.2023 | Helmond Sport - Den Bosch | 1 : 0 |
| 14.04.2023 | Den Bosch - Helmond Sport | 1 : 2 |
| 16.12.2022 | Helmond Sport - Den Bosch | 1 : 0 |
| 06.05.2022 | Helmond Sport - Den Bosch | 1 : 1 |
| 06.08.2021 | Den Bosch - Helmond Sport | 2 : 0 |
| Date | Match | Score | Res |
|---|---|---|---|
| 13.09.2026 | FC Volendam - Den Bosch | 2 - 0 | L |
| 07.09.2026 | Jong PSV U21 - Den Bosch | 3 - 1 | L |
| 28.08.2026 | Den Bosch - Vitesse | 1 - 4 | L |
| 21.08.2026 | Den Bosch - FC Eindhoven | 5 - 2 | W |
| 14.08.2026 | Heracles - Den Bosch | 3 - 2 | L |
| 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 |