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| 09/05/1959 | ADO | - | EDO Haarlem | 3:2 (2:2) | ||
| vv Heerenveen | - | VV Leeuwarden | 1:0 (1:0) | |||
| 10/05/1959 | AFC Ajax | - | De Volewijckers | 3:0 (1:0) | ||
| Enschedese Boys | - | HVV Hengelo | 1:0 (0:0) | |||
| HFC Haarlem | - | SHS | 2:3 (1:2, 2:2) aet | |||
| HVC Amersfoort | - | Alkmaar '54 | 6:0 (0:0) | |||
| NAC Breda | - | VV Hulst | 8:1 (1:1) | |||
| NOAD Tilburg | - | Hermes/DVS | 1:0 (0:0, 0:0) aet | |||
| Rapid JC Heerlen | - | RKSV Helmondia '55 | 4:1 (2:0) | |||
| SC Rheden | - | USV Elinkwijk | 1:2 (1:1, 1:1) aet | |||
| VVV | - | OSS '20 | 3:0 (3:0) | |||
| VV Zwartemeer | - | Groninger VAV | 1:0 (0:0) | |||
| 16/05/1959 | RC&FC Sparta | - | Celeritudo | 6:0 (2:0) | ||
| 20/05/1959 | RKVV Wilhelmina | - | Fortuna '54 | 2:5 (2:2) | ||
| 21/05/1959 | SC NEC | - | DOS Utrecht | 1:0 (0:0, 0:0, 0:0) pso | ||
| UVS | - | RKSV Volendam | 1:2 (1:1) |
