| 2024-05-03 20:00 | J37 | Helmond Sport |  | 2-0 |  | FC Eindhoven | | |
| 2024-04-19 20:00 | J35 | Helmond Sport | | 3-1 |  | Ajax B | Anthony van den Hurk 33' 42', Pius Krätschmer 65'; Tristan Gooijer 82' | |
| 2024-03-29 20:00 | J32 | Helmond Sport | | 0-2 |  | Willem II | Ringo Meerveld 39', Thijs Oosting 45' | |
| 2024-03-11 20:00 | J31 | Helmond Sport | | 3-1 |  | AZ Alkmaar B | Martijn Kaars 6', Giannis Fivos Botos 56', Álvaro Marín 62'; Ernest Poku 80' | |
| 2024-03-01 20:00 | J28 | Helmond Sport | | 1-1 |  | VVV-Venlo | Joeri Schroijen 63'; Thijme Verheijen 32' | |
| 2024-02-16 20:00 | J26 | Helmond Sport | | 3-1 |  | De Graafschap | Álvaro Marín 26' 43', Martijn Kaars 90'; Simon Colyn 18' | |
| 2024-01-26 20:00 | J23 | Helmond Sport | | 1-0 |  | NAC Breda | Martijn Kaars 90' | |
| 2024-01-19 20:00 | J22 | Helmond Sport | | 2-2 |  | PSV B | Giannis Fivos Botos 12', Anthony van den Hurk 36'; Jevon Simons 27', Wessel Kuhn 69' | |
| 2023-12-23 18:45 | J20 | Helmond Sport | | 3-3 |  | Roda | Giannis Fivos Botos 13' 28' 52'; Maximilian Schmid 32', Enrique Peña Zauner 51', Walid Ould-Chikh 90' | |
| 2023-12-08 20:00 | J18 | Helmond Sport | | 1-2 |  | MVV | Martijn Kaars 29'; Ferre Slegers 79', Dailon Rocha 90' | |
| 2023-12-01 20:00 | J17 | Helmond Sport | | 3-2 |  | ADO Den Haag | Arno Van Keilegom 4', Martijn Kaars 9' 80' (p.); Henk Veerman 23' 58' | |
| 2023-11-24 20:00 | J16 | Helmond Sport | | 1-2 |  | FC Emmen | Martijn Kaars 68' (p.); Ahmed El Messaoudi 24', Piotr Parzyszek 45' | |
| 2023-11-03 20:00 | J13 | Helmond Sport | | 1-0 |  | Telstar | Martijn Kaars 29' | |
| 2023-10-23 20:00 | J10 | Helmond Sport | | 1-1 |  | FC Dordrecht | Mohamed Mallahi 45'; Ilias Bronkhorst 47' | |
| 2023-10-06 20:00 | J9 | Helmond Sport | | 4-0 |  | FC Utrecht B | Martijn Kaars 4' 68', Joseph Amuzu 13', Giannis Fivos Botos 52' | |
| 2023-09-22 20:00 | J7 | Helmond Sport | | 1-2 |  | FC Groningen | Martijn Kaars 87' (p.); Thom van Bergen 71', Liam van Gelderen 90' | |
| 2023-09-15 20:00 | J6 | Helmond Sport | | 1-1 |  | TOP Oss | Michael Chacón 55'; Delano Ladan 90' | |
| 2023-09-01 20:00 | J4 | Helmond Sport | | 2-1 |  | SC Cambuur | Martijn Kaars 48' 90'; Milan Smit 70' | |
| 2023-08-18 20:00 | J2 | Helmond Sport | | 1-0 |  | Den Bosch | Giannis Fivos Botos 27' | |
