| 14 May 2023 | First Round | Chellaston v Sandiacre Town Second XI | Moira Dale, Castle Donington | Results |
| 29 May 2023 | First Round | Chesterfield v Marehay | Queen's Park, Chesterfield | Results |
| 14 May 2023 | First Round | Elvaston v Mickleover | Stable Drive, Elvaston | Results |
| 21 May 2023 | First Round | Sawley v Duffield | West Park, Long Eaton | Results |
| 14 May 2023 | First Round | Tutbury v Ilkeston Rutland | Tutbury Mill, Tutbury | Results |
| 14 May 2023 | First Round | Wirksworth and Middleton v Ockbrook and Borrowash Second XI | The Recreation Ground, Wirksworth | Results |
| 11 Jun 2023 | Second Round | Ilkeston Rutland v Sandiacre Town Second XI | Rutland Recreation Ground, Ilkeston | Results |
| 11 Jun 2023 | Second Round | Sawley v Chesterfield | West Park, Long Eaton | Results |
| 11 Jun 2023 | Second Round | South Wingfield v Mickleover | Holme Lane, South Wingfield | Results |
| 11 Jun 2023 | Second Round | Shipley Hall v Clifton | The Field, Shipley | Results |
| 11 Jun 2023 | Second Round | Denby Second XI v Clowne Town | The Copper Yard, Denby Village | Results |
| 11 Jun 2023 | Second Round | Langley Mill United v Belper Meadows | Station Road, Langley Mill | Results |
| 11 Jun 2023 | Second Round | Spondon Second XI v Morton Colliery | Locko Road, Spondon | Results |
| 11 Jun 2023 | Second Round | Ockbrook and Borrowash Second XI v Derby Congregational | Victoria Avenue, Ockbrook | Results |
| 09 Jul 2023 | Quarter-Final | South Wingfield v Shipley Hall | Holme Lane, South Wingfield | Results |
| 02 Jul 2023 | Quarter-Final | Clowne Town v Belper Meadows | High Leys Road, Clowne | Results |
| 02 Jul 2023 | Quarter-Final | Ilkeston Rutland v Chesterfield | Rutland Recreation Ground, Ilkeston | Results |
| 02 Jul 2023 | Quarter-Final | Morton Colliery v Derby Congregational | Back Lane, Morton | Results |
| 30 Jul 2023 | Semi-Final | Chesterfield v South Wingfield | Queen's Park, Chesterfield | Results |
| 30 Jul 2023 | Semi-Final | Belper Meadows v Morton Colliery | Christchurch Meadows, Belper | Results |
| 28 Aug 2023 | Final | Morton Colliery v South Wingfield | Queen's Park, Chesterfield | Results |
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