| 02 Jun 2002 | First Round | Alfreton v Marehay | Alfreton Park, Alfreton | Results |
| 02 Jun 2002 | First Round | Aston-on-Trent v Brailsford and Ednaston | Shardlow Road, Aston-on-Trent | Results |
| 02 Jun 2002 | First Round | Denby Second XI v Selston Town | The Copper Yard, Denby Village | Results |
| 02 Jun 2002 | First Round | Little Eaton v Allestree | St Peters Park, Little Eaton | Results |
| 02 Jun 2002 | First Round | Mickleover v Nutbrook | Station Road, Mickleover | Results |
| 02 Jun 2002 | First Round | Rolleston v West Hallam White Rose | Dovecliff Road, Rolleston-on-Dove | Results |
| 02 Jun 2002 | First Round | Sandiacre Town Second XI v Duffield | Longmoor Lane, Sandiacre | Results |
| 02 Jun 2002 | First Round | Ticknall v Ockbrook and Borrowash Second XI | The Grange, Ticknall | Results |
| 16 Jun 2002 | Second Round | Belper Meadows v Duffield | Christchurch Meadows, Belper | Results |
| 16 Jun 2002 | Second Round | Elvaston v Aston-on-Trent | Stable Drive, Elvaston | Results |
| 16 Jun 2002 | Second Round | Lullington Park v Alfreton | Lullington Park Pitch 2, Lullington | Results |
| 16 Jun 2002 | Second Round | Nutbrook v Morton Colliery | Nutbrook Sports Ground, West Hallam | Results |
| 16 Jun 2002 | Second Round | Ockbrook and Borrowash Second XI v Spondon | Victoria Avenue, Ockbrook | Results |
| 16 Jun 2002 | Second Round | Selston Town v Staveley Welfare | The Parish Hall Ground, Selston | Results |
| 16 Jun 2002 | Second Round | Shipley Hall v Allestree | The Field, Shipley | Results |
| 16 Jun 2002 | Second Round | West Hallam White Rose v Stainsby Hall | Beech Lane, West Hallam | Results |
| 07 Jul 2002 | Quarter-Final | Aston-on-Trent v Selston Town | Shardlow Road, Aston-on-Trent | Results |
| 07 Jul 2002 | Quarter-Final | Lullington Park v Shipley Hall | Lullington Park Pitch 2, Lullington | Results |
| 07 Jul 2002 | Quarter-Final | Morton Colliery v West Hallam White Rose | Back Lane, Morton | Results |
| 07 Jul 2002 | Quarter-Final | Spondon v Belper Meadows | Locko Road, Spondon | Results |
| 28 Jul 2002 | Semi-Final | Spondon v Aston-on-Trent | Locko Road, Spondon | Results |
| 28 Jul 2002 | Semi-Final | West Hallam White Rose v Lullington Park | Beech Lane, West Hallam | Results |
| 11 Aug 2002 | Final | Lullington Park v Spondon | The Copper Yard, Denby Village | Results |
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