| 06 Jun 2021 | First Round | Ambergate Second XI v Buxton Second XI | The Hurt Arms Ground, Ambergate | Results |
| 06 Jun 2021 | First Round | Clifton Second XI v Darley Abbey Second XI | Chapel Lane, Clifton | Results |
| 06 Jun 2021 | First Round | Denby Third XI v Swanwick Hall | Riddings Park, Riddings | Results |
| 06 Jun 2021 | First Round | Hartshorne v Tutbury Second XI | Faldo Close, Branston | Results |
| 06 Jun 2021 | First Round | Denby Third XI v Marehay Third XI | Riddings Park, Riddings | Results |
| 06 Jun 2021 | First Round | Allestree v Ockbrook and Borrowash Third XI | Locko Road, Spondon | Results |
| 06 Jun 2021 | First Round | Pilsley and Clay Cross v Shipley Hall Second XI | Pilsley Parish Sports Ground, Pilsley | Results |
| 06 Jun 2021 | First Round | Riddings v Swanwick Hall | Riddings Park, Riddings | Results |
| 06 Jun 2021 | First Round | Spondon Fourth XI v Kirk Langley | Locko Road, Spondon | Results |
| 06 Jun 2021 | First Round | Trentside Second XI v Chellaston Third XI | Faldo Close, Branston | Results |
| 27 Jun 2021 | First Round | Selston Town v Heanor Town | The Parish Hall Ground, Selston | Results |
| 06 Jun 2021 | Second Round | Ambergate Second XI v Belper Meadows Second XI | The Hurt Arms Ground, Ambergate | Results |
| 06 Jun 2021 | Second Round | Duffield Second XI v Clifton Second XI | Eyes Meadow, Duffield | Results |
| 06 Jun 2021 | Second Round | Kirk Langley v Ockbrook and Borrowash Third XI | Locko Road, Spondon | Results |
| 06 Jun 2021 | Second Round | Pilsley and Clay Cross v Butterley United | Pilsley Parish Sports Ground, Pilsley | Results |
| 06 Jun 2021 | Second Round | Rosehill Methodists v Ashbourne | Littleover Lane Cricket Ground, Littleover | Results |
| 16 Jun 2021 | Second Round | Marehay Third XI v Swanwick Hall | The Maryfield, Ripley | Results |
| 17 Jun 2021 | Second Round | Duffield Second XI v Darley Abbey Second XI | Eyes Meadow, Duffield | Results |
| 27 Jun 2021 | Second Round | Selston Town v Nutbrook Second XI | The Parish Hall Ground, Selston | Results |
| 11 Jul 2021 | Quarter-Final | Ambergate Second XI v Pilsley and Clay Cross | The Hurt Arms Ground, Ambergate | Results |
| 11 Jul 2021 | Quarter-Final | Darley Abbey Second XI v Hartshorne | Victoria Avenue Pitch 2, Ockbrook | Results |
| 11 Jul 2021 | Quarter-Final | Ockbrook and Borrowash Third XI v Rosehill Methodists | Victoria Avenue Pitch 2, Ockbrook | Results |
| 11 Jul 2021 | Quarter-Final | Selston Town v Swanwick Hall | The Hurt Arms Ground, Ambergate | Results |
| 18 Jul 2021 | Semi-Final | Ambergate Second XI v Selston Town | The Hurt Arms Ground, Ambergate | Results |
| 21 Jul 2021 | Semi-Final | Darley Abbey Second XI v Ockbrook and Borrowash Third XI | Riverside Meadow, Darley Abbey | Results |
| 01 Aug 2021 | Final | Ockbrook and Borrowash Third XI v Selston Town | The Field, Shipley | Results |
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