| 06 Jun 2021 | First Round | Brailsford and Ednaston v Rolleston Second XI | Pools Head Lane, Brailsford | Results |
| 06 Jun 2021 | First Round | Burton v Tutbury | The Town Ground, Burton-on-Trent | Results |
| 06 Jun 2021 | First Round | Buxton v Chesterfield Second XI | The Park, Buxton | Results |
| 06 Jun 2021 | First Round | Marehay Second XI v Alfreton Second XI | The Maryfield, Ripley | Results |
| 06 Jun 2021 | First Round | Nutbrook v Stainsby Hall Second XI | Nutbrook Sports Ground, West Hallam | Results |
| 06 Jun 2021 | First Round | Winshill v Sawley Second XI | Mill Hill Lane, Winshill | Results |
| 06 Jun 2021 | Second Round | Brailsford and Ednaston v Uttoxeter | Pools Head Lane, Brailsford | Results |
| 06 Jun 2021 | Second Round | Alvaston and Boulton Second XI v Spondon Third XI | Raynesway, Alvaston | Results |
| 06 Jun 2021 | Second Round | Chesterfield Second XI v Hundall | Queen's Park, Chesterfield | Results |
| 06 Jun 2021 | Second Round | Marehay Second XI v Denby Second XI | The Maryfield, Ripley | Results |
| 06 Jun 2021 | Second Round | Nutbrook v Langley Mill United Second XI | Nutbrook Sports Ground, West Hallam | Results |
| 06 Jun 2021 | Second Round | West Hallam White Rose v Belper Amateurs | Cock Orchard, West Hallam | Results |
| 06 Jun 2021 | Second Round | Winshill v Chellaston Second XI | Mill Hill Lane, Winshill | Results |
| 06 Jun 2021 | Second Round | Burton v Etwall | The Town Ground, Burton-on-Trent | Results |
| 11 Jul 2021 | Quarter-Final | Belper Amateurs v Chesterfield Second XI | Christchurch Meadows, Belper | Results |
| 11 Jul 2021 | Quarter-Final | Brailsford and Ednaston v Winshill | The Town Ground, Burton-on-Trent | Results |
| 11 Jul 2021 | Quarter-Final | Burton v Spondon Third XI | The Town Ground, Burton-on-Trent | Results |
| 11 Jul 2021 | Quarter-Final | Marehay Second XI v Nutbrook | Christchurch Meadows, Belper | Results |
| 16 Jul 2021 | Semi-Final | Winshill v Burton | Mill Hill Lane, Winshill | Results |
| 18 Jul 2021 | Semi-Final | Belper Amateurs v Nutbrook | The Packhorse Ground, Alderwasley | Results |
| 01 Aug 2021 | Final | Burton v Nutbrook | The Field, Shipley | Results |
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