| 1. Round | 23/08/1959 | RKSV Volendam | - | DWS Amsterdam | 3:1 | ||||
| 2. Round | 30/08/1959 | DOS Utrecht | - | RKSV Volendam | 2:0 | ||||
| 3. Round | 06/09/1959 | RKSV Sittardia | - | RKSV Volendam | 1:5 |  |
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| 4. Round | 13/09/1959 | RKSV Volendam | - | Sportclub Enschede | 2:1 | ||||
| 5. Round | 20/09/1959 | RC&FC Sparta | - | RKSV Volendam | 3:2 | |
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| 6. Round | 27/09/1959 | RKSV Volendam | - | VVV | 1:2 | ||||
| 7. Round | 11/10/1959 | Blauw Wit | - | RKSV Volendam | 2:3 | ||||
| 8. Round | 18/10/1959 | RKSV Volendam | - | Rapid JC Heerlen | 2:1 | ||||
| 9. Round | 25/10/1959 | RKSV Volendam | - | Feijenoord | 1:1 | ||||
| 10. Round | 01/11/1959 | ADO | - | RKSV Volendam | 4:1 | ||||
| 12. Round | 15/11/1959 | Fortuna '54 | - | RKSV Volendam | 4:2 | ||||
| 13. Round | 22/11/1959 | RKSV Volendam | - | AFC Ajax | 0:3 | ||||
| 27. Round | 20/03/1960 | RKSV Volendam | - | ADO | 0:2 | ||||
| 28. Round | 27/03/1960 | USV Elinkwijk | - | RKSV Volendam | 3:2 | ||||
| 29. Round | 10/04/1960 | RKSV Volendam | - | Fortuna '54 | 0:4 | ||||
| 30. Round | 18/04/1960 | AFC Ajax | - | RKSV Volendam | 9:0 | ||||
| 34. Round | 22/05/1960 | Willem II | - | RKSV Volendam | 2:1 |
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