 | 16 May 1959 | First Round | | Barrow v Furness | Ernest Pass Memorial Ground, Barrow-in-Furness | misc862540 |
| 16 May 1959 | First Round | | Carnforth v Carlisle | Lodge Quarry, Carnforth | misc862543 |
| 16 May 1959 | First Round | | Millom v Dalton | St George's Road, Millom | misc862541 |
| 16 May 1959 | First Round | | Millom Iron Works v Lindal Moor | Coronation Field, Millom | misc862544 |
| 16 May 1959 | First Round | | Penrith v Workington | Tynefield Park, Penrith | misc846367 |
| 16 May 1959 | First Round | | Ulverston v Haverigg | Tarn Close, Ulverston | misc862542 |
| 28 May 1959 | First Round | | Vickerstown v Whitehaven | Rainey Park, Barrow-in-Furness | misc862545 |
| 13 Jun 1959 | Second Round | | Carlisle v Furness | Edenside, Carlisle | misc862546 |
| 13 Jun 1959 | Second Round | | Dalton v Lindal Moor | Ulverston Road, Dalton-in-Furness | misc862547 |
| 13 Jun 1959 | Second Round | | Whitehaven v Vickers Sports Club | The Playground, Whitehaven | misc862548 |
| 13 Jun 1959 | Second Round | | Workington v Ulverston | Ernest Valentine Ground, Workington | misc862549 |
| 24 Jul 1959 | Semi-Final | | Whitehaven v Ulverston | The Playground, Whitehaven | misc |
| 29 Jul 1959 | Semi-Final | | Carlisle v Lindal Moor | Edenside, Carlisle | misc862551 |
| 06 Aug 1959 | Final | | Carlisle v Whitehaven | St George's Road, Millom | misc810590 |
