| 09 May 2010 | First Round | Belper Meadows v Sandiacre Town Second XI | Christchurch Meadows, Belper | Results |
| 09 May 2010 | First Round | Chesterfield Second XI v Denby | Queen's Park, Chesterfield | Results |
| 09 May 2010 | First Round | Clay Cross v Spondon Second XI | Sharley Park, Clay Cross | Results |
| 09 May 2010 | First Round | Cutthorpe v Staveley Welfare | Cutthorpe Park, Cutthorpe | Results |
| 09 May 2010 | First Round | Darley Dale v Aston-on-Trent | Station Road, South Darley | Results |
| 09 May 2010 | First Round | Denby Second XI v Trentside | The Copper Yard, Denby Village | Results |
| 09 May 2010 | First Round | Lullington Park Second XI v Walton-on-Trent | Lullington Park Pitch 2, Lullington | Results |
| 09 May 2010 | First Round | Marehay v Ambergate | The Maryfield, Ripley | Results |
| 09 May 2010 | First Round | Ockbrook and Borrowash Second XI v Swarkestone | Victoria Avenue, Ockbrook | Results |
| 09 May 2010 | First Round | Rolls Royce v South Wingfield | Rolls Royce Ground, Derby | Results |
| 09 May 2010 | First Round | Sawley and Long Eaton Park v Clifton | West Park, Long Eaton | Results |
| 09 May 2010 | First Round | Stainsby Hall v Derby Congregational | St Johns Road, Smalley | Results |
| 09 May 2010 | First Round | Ticknall v Heanor Town | The Grange, Ticknall | Results |
| 09 May 2010 | First Round | Tutbury v Langley Mill United | Tutbury Mill, Tutbury | Results |
| 06 Jun 2010 | Second Round | Clay Cross v Langley Mill United | Sharley Park, Clay Cross | Results |
| 06 Jun 2010 | Second Round | Clifton v Walton-on-Trent | Chapel Lane, Clifton | Results |
| 06 Jun 2010 | Second Round | Cutthorpe v Nutbrook | Cutthorpe Park, Cutthorpe | Results |
| 06 Jun 2010 | Second Round | Darley Dale v Swarkestone | Station Road, South Darley | Results |
| 06 Jun 2010 | Second Round | Rolleston v Denby | Dovecliff Road, Rolleston-on-Dove | Results |
| 06 Jun 2010 | Second Round | Rolls Royce v Denby Second XI | Rolls Royce Ground, Derby | Results |
| 06 Jun 2010 | Second Round | Sandiacre Town Second XI v Ticknall | Longmoor Lane, Sandiacre | Results |
| 06 Jun 2010 | Second Round | Stainsby Hall v Marehay | St Johns Road, Smalley | Results |
| 04 Jul 2010 | Quarter-Final | Clay Cross v Ticknall | Sharley Park, Clay Cross | Results |
| 04 Jul 2010 | Quarter-Final | Clifton v Swarkestone | Chapel Lane, Clifton | Results |
| 04 Jul 2010 | Quarter-Final | Cutthorpe v Rolls Royce | Cutthorpe Park, Cutthorpe | Results |
| 04 Jul 2010 | Quarter-Final | Denby v Marehay | The Copper Yard, Denby Village | Results |
| 18 Jul 2010 | Semi-Final | Denby v Ticknall | The Copper Yard, Denby Village | Results |
| 18 Jul 2010 | Semi-Final | Swarkestone v Rolls Royce | Barrow Turn, Swarkestone | Results |
| 30 Aug 2010 | Final | Denby v Rolls Royce | Locko Road, Spondon | Results |
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