| 1. Round | 03/08/2019 | FC Twente | - | PSV Eindhoven | 1:1 | ||||
| 2. Round | 11/08/2019 | PSV Eindhoven | - | ADO Den Haag | 3:1 | ||||
| 3. Round | 18/08/2019 | Heracles Almelo | - | PSV Eindhoven | 0:2 |  |
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| 7. Round | 22/09/2019 | PSV Eindhoven | - | AFC Ajax | 1:1 | |
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| 4. Round | 25/09/2019 | PSV Eindhoven | - | FC Groningen | 3:1 | ||||
| 8. Round | 29/09/2019 | PEC Zwolle | - | PSV Eindhoven | 0:4 | ||||
| 9. Round | 06/10/2019 | PSV Eindhoven | - | VVV-Venlo | 4:1 | ||||
| 10. Round | 19/10/2019 | FC Utrecht | - | PSV Eindhoven | 3:0 | ||||
| 11. Round | 27/10/2019 | PSV Eindhoven | - | AZ Alkmaar | 0:4 | ||||
| 12. Round | 02/11/2019 | Sparta Rotterdam | - | PSV Eindhoven | 2:2 |  |
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| 13. Round | 10/11/2019 | Willem II | - | PSV Eindhoven | 2:1 | ||||
| 14. Round | 24/11/2019 | PSV Eindhoven | - | sc Heerenveen | 2:1 | ||||
| 15. Round | 01/12/2019 | FC Emmen | - | PSV Eindhoven | 1:1 | |
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| 16. Round | 07/12/2019 | PSV Eindhoven | - | Fortuna Sittard | 5:0 |
Czech Republic