| 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 |  |
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| 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 | ||||
| 7. Round | 26/10/2019 | Almere City FC [Youth] | - | PSV Eindhoven [Youth] | 3:2 | ||||
| 11. Round | 30/11/2019 | PSV Eindhoven [Youth] | - | Vitesse [Youth] | 5:1 |  |
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| 8. Round | 03/12/2019 | AZ Alkmaar [Youth] | - | PSV Eindhoven [Youth] | 0:3 | ||||
| 12. Round | 07/12/2019 | NAC Breda [Youth] | - | PSV Eindhoven [Youth] | 2:0 | ||||
| 13. Round | 14/12/2019 | PSV Eindhoven [Youth] | - | Feyenoord [Youth] | 3:0 |
Netherlands