| 30 May 2021 | First Round | Belper Amateurs Second XI v Belper Meadows Third XI | The Packhorse Ground, Alderwasley | Results |
| 30 May 2021 | First Round | Castle Donington Town v Burton Second XI | Moira Dale, Castle Donington | Results |
| 30 May 2021 | First Round | Ilkeston Rutland Third XI v Riddings Second XI | The Stute, Ilkeston | Results |
| 30 May 2021 | First Round | Stainsby Hall Second XI v Swanwick Hall Second XI | St Johns Road, Smalley | Results |
| 30 May 2021 | First Round | Staveley Welfare v Chesterfield Third XI | Lowgates, Staveley | Results |
| 30 May 2021 | First Round | Uttoxeter Second XI v Ockbrook and Borrowash Fourth XI | Jacks Lane Cricket Ground, Marchington | Results |
| 30 May 2021 | Second Round | Belper Amateurs Second XI v Nutbrook Third XI | The Packhorse Ground, Alderwasley | Results |
| 30 May 2021 | Second Round | Buxton Third XI v Chesterfield Third XI | Lowgates, Staveley | Results |
| 30 May 2021 | Second Round | Clifton Third XI v Ockbrook and Borrowash Fourth XI | Jacks Lane Cricket Ground, Marchington | Results |
| 30 May 2021 | Second Round | Denby Fourth XI v Langley Mill United Third XI | The Copper Yard Pitch 2, Denby Village | Results |
| 30 May 2021 | Second Round | Ilkeston Rutland Third XI v South Wingfield Third XI | The Stute, Ilkeston | Results |
| 30 May 2021 | Second Round | Sawley Third XI v Winshill Second XI | West Park Pitch 2, Long Eaton | Results |
| 30 May 2021 | Second Round | Duffield Third XI v Swanwick Hall Second XI | St Johns Road, Smalley | Results |
| 06 Jun 2021 | Second Round | Castle Donington Town v Mickleover Third XI | Moira Dale, Castle Donington | Results |
| 04 Jul 2021 | Quarter-Final | Belper Amateurs Second XI v Chesterfield Third XI | The Packhorse Ground, Alderwasley | Results |
| 04 Jul 2021 | Quarter-Final | Denby Fourth XI v Swanwick Hall Second XI | The Packhorse Ground, Alderwasley | Results |
| 04 Jul 2021 | Quarter-Final | Ockbrook and Borrowash Fourth XI v Ilkeston Rutland Third XI | Victoria Avenue Pitch 2, Ockbrook | Results |
| 22 Jul 2021 | Quarter-Final | Winshill Second XI v Castle Donington Town | Mill Hill Lane, Winshill | Results |
| 14 Jul 2021 | Semi-Final | Denby Fourth XI v Chesterfield Third XI | The Copper Yard, Denby Village | Results |
| 25 Jul 2021 | Semi-Final | Ockbrook and Borrowash Fourth XI v Castle Donington Town | Victoria Avenue Pitch 2, Ockbrook | Results |
| 30 Aug 2021 | Final | Denby Fourth XI v Ockbrook and Borrowash Fourth XI | Riverside Meadow, Darley Abbey | Results |
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