| 18 May 2008 | Preliminary Round | Quarndon Second XI v Alvaston and Boulton Second XI | The Common, Quarndon | Results |
| 01 Jun 2008 | First Round | Allestree v Aston-on-Trent | The Recreation Ground, Allestree | Results |
| 01 Jun 2008 | First Round | Brailsford and Ednaston v Alvaston and Boulton Second XI | Pools Head Lane, Brailsford | Results |
| 01 Jun 2008 | First Round | Clifton v Chesterfield Second XI | Chapel Lane, Clifton | Results |
| 01 Jun 2008 | First Round | Derby Congregational v Rolleston | Brayfield Road, Littleover | Results |
| 01 Jun 2008 | First Round | Rolls Royce v Duffield | Rolls Royce Ground, Derby | Results |
| 01 Jun 2008 | First Round | Trentside v Wirksworth and Middleton | Faldo Close, Branston | Results |
| 01 Jun 2008 | First Round | Tutbury v Staveley Welfare | Tutbury Mill, Tutbury | Results |
| 08 Jun 2008 | First Round | Ambergate v Clay Cross | The Hurt Arms Ground, Ambergate | Results |
| 08 Jun 2008 | First Round | Belper Amateurs v Belper Meadows | The Packhorse Ground, Alderwasley | Results |
| 08 Jun 2008 | First Round | Darley Dale v Barton-under-Needwood | Station Road, South Darley | Results |
| 08 Jun 2008 | First Round | Denby v Spondon Second XI | The Copper Yard, Denby Village | Results |
| 08 Jun 2008 | First Round | Marehay v South Wingfield | The Maryfield, Ripley | Results |
| 08 Jun 2008 | First Round | Matlock v Denby Second XI | Causeway Lane, Matlock | Results |
| 08 Jun 2008 | First Round | Ockbrook and Borrowash Second XI v Swarkestone | Victoria Avenue, Ockbrook | Results |
| 08 Jun 2008 | First Round | Sandiacre Town Second XI v Nutbrook | Longmoor Lane, Sandiacre | Results |
| 08 Jun 2008 | First Round | Stainsby Hall v Sawley and Long Eaton Park | St Johns Road, Smalley | Results |
| 15 Jun 2008 | Second Round | Ambergate v Denby | The Hurt Arms Ground, Ambergate | Results |
| 15 Jun 2008 | Second Round | Belper Meadows v Swarkestone | Christchurch Meadows, Belper | Results |
| 15 Jun 2008 | Second Round | Derby Congregational v Nutbrook | Brayfield Road, Littleover | Results |
| 15 Jun 2008 | Second Round | Marehay v Clifton | The Maryfield, Ripley | Results |
| 15 Jun 2008 | Second Round | Matlock v Rolls Royce | Causeway Lane, Matlock | Results |
| 15 Jun 2008 | Second Round | Stainsby Hall v Darley Dale | St Johns Road, Smalley | Results |
| 15 Jun 2008 | Second Round | Staveley Welfare v Alvaston and Boulton Second XI | Lowgates, Staveley | Results |
| 15 Jun 2008 | Second Round | Trentside v Aston-on-Trent | Faldo Close, Branston | Results |
| 29 Jun 2008 | Quarter-Final | Denby v Belper Meadows | The Copper Yard, Denby Village | Results |
| 29 Jun 2008 | Quarter-Final | Staveley Welfare v Aston-on-Trent | Lowgates, Staveley | Results |
| 13 Jul 2008 | Quarter-Final | Derby Congregational v Clifton | Brayfield Road, Littleover | Results |
| 13 Jul 2008 | Quarter-Final | Rolls Royce v Stainsby Hall | Rolls Royce Ground, Derby | Results |
| 20 Jul 2008 | Semi-Final | Aston-on-Trent v Rolls Royce | Shardlow Road, Aston-on-Trent | Results |
| 20 Jul 2008 | Semi-Final | Denby v Clifton | The Copper Yard, Denby Village | Results |
| 25 Aug 2008 | Final | Aston-on-Trent v Clifton | The Grange, Ticknall | Results |
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