| 1. Round | 03/08/2019 | FC Twente | - | PSV Eindhoven | 1:1 | ||||
| 3. Round | 18/08/2019 | Heracles Almelo | - | PSV Eindhoven | 0:2 |  |
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| 5. Round | 01/09/2019 | RKC Waalwijk | - | PSV Eindhoven | 1:3 | ||||
| 6. Round | 14/09/2019 | PSV Eindhoven | - | Vitesse | 5:0 | ||||
| 7. Round | 22/09/2019 | PSV Eindhoven | - | AFC Ajax | 1:1 | ||||
| 4. Round | 25/09/2019 | PSV Eindhoven | - | FC Groningen | 3:1 | ||||
| 11. Round | 27/10/2019 | PSV Eindhoven | - | AZ Alkmaar | 0:4 | ||||
| 12. Round | 02/11/2019 | Sparta Rotterdam | - | PSV Eindhoven | 2:2 | ||||
| 17. Round | 15/12/2019 | Feyenoord | - | PSV Eindhoven | 3:1 | ||||
| 19. Round | 19/01/2020 | VVV-Venlo | - | PSV Eindhoven | 1:1 | ||||
| 21. Round | 02/02/2020 | AFC Ajax | - | PSV Eindhoven | 1:0 | ||||
| 26. Round | 08/03/2020 | FC Groningen | - | PSV Eindhoven | 0:1 |
Monaco