| 1. Round | 14/09/2019 | PSV Eindhoven [Youth] | - | ADO Den Haag [Youth] | 2:1 | ||||
| 2. Round | 21/09/2019 | FC Utrecht [Youth] | - | PSV Eindhoven [Youth] | 0:1 | ||||
| 3. Round | 24/09/2019 | PSV Eindhoven [Youth] | - | Sparta Rotterdam [Youth] | 3:0 | ||||
| 4. Round | 28/09/2019 | AFC Ajax [Youth] | - | PSV Eindhoven [Youth] | 3:4 |  |
|||
| 5. Round | 05/10/2019 | PSV Eindhoven [Youth] | - | NEC/FC Oss [Youth] | 3:0 |  |
|||
| 6. Round | 19/10/2019 | PSV Eindhoven [Youth] | - | FC Twente [Youth] | 2:1 | |
|||
| 9. Round | 09/11/2019 | PSV Eindhoven [Youth] | - | sc Heerenveen [Youth] | 0:2 | |
|||
| 10. Round | 23/11/2019 | FC Groningen [Youth] | - | PSV Eindhoven [Youth] | 1:0 | |
|||
| 11. Round | 30/11/2019 | PSV Eindhoven [Youth] | - | Vitesse [Youth] | 5:1 | ||||
| 8. Round | 03/12/2019 | AZ Alkmaar [Youth] | - | PSV Eindhoven [Youth] | 0:3 |
Netherlands