| 4. Round | 15/09/2019 | OSS '20 | - | RKVV Westlandia | 5:0 | ||||
| 5. Round | 21/09/2019 | VV UNA | - | OSS '20 | 2:2 | ||||
| 6. Round | 29/09/2019 | OSS '20 | - | OFC Oostzaan | 2:2 | ||||
| 8. Round | 13/10/2019 | RKVV DEM | - | OSS '20 | 1:3 | ||||
| 9. Round | 26/10/2019 | OSS '20 | - | HSC'21 | 3:2 | ||||
| 10. Round | 02/11/2019 | Blauw Geel '38 | - | OSS '20 | 0:1 | ||||
| 12. Round | 17/11/2019 | Quick Den Haag | - | OSS '20 | 1:2 | ||||
| 14. Round | 01/12/2019 | EVV | - | OSS '20 | 0:1 | ||||
| 15. Round | 08/12/2019 | FC Lienden | - | OSS '20 | 1:4 | ||||
| 16. Round | 15/12/2019 | OSS '20 | - | USV Hercules | 4:2 | ||||
| 19. Round | 26/01/2020 | ADO '20 | - | OSS '20 | 1:1 | ||||
| 20. Round | 02/02/2020 | OSS '20 | - | Blauw Geel '38 | 3:2 | ||||
| 23. Round | 01/03/2020 | HSC'21 | - | OSS '20 | 0:3 | ||||
| 24. Round | 08/03/2020 | OSS '20 | - | RKSV Groene Ster | 3:1 |
Netherlands