| District Zuid II | 01/01/1959 | RKVV Tiglia | - | VVV | 2:14 |  |
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| 3. Round | 10/05/1959 | VVV | - | OSS '20 | 3:0 | ||||
| Round of 16 | 28/05/1959 | VVV | - | Enschedese Boys | 7:1 | |
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| Quarter-finals | 06/06/1959 | VVV | - | VV Zwartemeer | 5:1 | ||||
| Semi-finals | 10/06/1959 | VVV | - | Rapid JC Heerlen | 1:0 | ||||
| Final | 17/06/1959 | ADO | - | VVV | 1:4 | |
Netherlands