| 10 May 2009 | First Round | Ambergate v Denby Second XI | The Hurt Arms Ground, Ambergate | Results |
| 10 May 2009 | First Round | Breadsall v West Hallam White Rose | Brookside Road, Breadsall | Results |
| 10 May 2009 | First Round | Clifton v Clay Cross | Chapel Lane, Clifton | Results |
| 10 May 2009 | First Round | Denby v Elvaston | The Copper Yard, Denby Village | Results |
| 10 May 2009 | First Round | Derby Congregational v Staveley Welfare | Brayfield Road, Littleover | Results |
| 10 May 2009 | First Round | Eckington v Spondon Second XI | Staveley Lane, Eckington | Results |
| 10 May 2009 | First Round | Heanor Town v Quarndon Second XI | Town Ground, Heanor | Results |
| 10 May 2009 | First Round | Nutbrook v Belper Meadows | Nutbrook Sports Ground, West Hallam | Results |
| 10 May 2009 | First Round | Rolleston v Sawley and Long Eaton Park | Dovecliff Road, Rolleston-on-Dove | Results |
| 10 May 2009 | First Round | Sandiacre Town Second XI v Lullington Park Second XI | Longmoor Lane, Sandiacre | Results |
| 10 May 2009 | First Round | South Wingfield v Ockbrook and Borrowash Second XI | Holme Lane, South Wingfield | Results |
| 10 May 2009 | First Round | Ticknall v Swarkestone | The Grange, Ticknall | Results |
| 10 May 2009 | First Round | Trentside v Darley Dale | Faldo Close, Branston | Results |
| 10 May 2009 | First Round | Tutbury v Cutthorpe | Tutbury Mill, Tutbury | Results |
| 14 Jun 2009 | Second Round | Belper Meadows v Denby | Christchurch Meadows, Belper | Results |
| 14 Jun 2009 | Second Round | Breadsall v Ticknall | Brookside Road, Breadsall | Results |
| 14 Jun 2009 | Second Round | Clifton v Lullington Park Second XI | Chapel Lane, Clifton | Results |
| 14 Jun 2009 | Second Round | Cutthorpe v Heanor Town | Cutthorpe Park, Cutthorpe | Results |
| 14 Jun 2009 | Second Round | Denby Second XI v Ockbrook and Borrowash Second XI | The Copper Yard, Denby Village | Results |
| 14 Jun 2009 | Second Round | Sawley and Long Eaton Park v Spondon Second XI | West Park, Long Eaton | Results |
| 14 Jun 2009 | Second Round | Staveley Welfare v Matlock | Lowgates, Staveley | Results |
| 14 Jun 2009 | Second Round | Trentside v Marehay | Faldo Close, Branston | Results |
| 28 Jun 2009 | Quarter-Final | Clifton v Denby Second XI | Chapel Lane, Clifton | Results |
| 28 Jun 2009 | Quarter-Final | Cutthorpe v Sawley and Long Eaton Park | Cutthorpe Park, Cutthorpe | Results |
| 28 Jun 2009 | Quarter-Final | Denby v Marehay | The Copper Yard, Denby Village | Results |
| 28 Jun 2009 | Quarter-Final | Matlock v Ticknall | Causeway Lane, Matlock | Results |
| 02 Aug 2009 | Semi-Final | Clifton v Marehay | Chapel Lane, Clifton | Results |
| 09 Aug 2009 | Semi-Final | Ticknall v Sawley and Long Eaton Park | The Grange, Ticknall | Results |
| 31 Aug 2009 | Final | Clifton v Ticknall | Lowgates, Staveley | Results |
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