| 30 Apr 2006 | Preliminary Round | Chesterfield Second XI v Heanor Town | Queen's Park, Chesterfield | Results |
| 30 Apr 2006 | Preliminary Round | Sawley and Long Eaton Park Second XI v Sandiacre Town Second XI | West Park, Long Eaton | Results |
| 30 Apr 2006 | Preliminary Round | Shipley Hall v Ockbrook and Borrowash Second XI | The Field, Shipley | Results |
| 28 May 2006 | First Round | Aston-on-Trent v Brailsford and Ednaston | Shardlow Road, Aston-on-Trent | Results |
| 28 May 2006 | First Round | Barton-under-Needwood v Belper Meadows | Holland Park Sports Club Ground, Barton-under-Needwood | Results |
| 28 May 2006 | First Round | Nutbrook v South Wingfield | Nutbrook Sports Ground, West Hallam | Results |
| 28 May 2006 | First Round | Pilsley v Duffield | Pilsley Parish Sports Ground, Pilsley | Results |
| 28 May 2006 | First Round | Riddings v Quarndon Second XI | Riddings Park, Riddings | Results |
| 28 May 2006 | First Round | Rolls Royce v Burton | Rolls Royce Ground, Derby | Results |
| 28 May 2006 | First Round | Spondon Second XI v Matlock | Locko Road, Spondon | Results |
| 28 May 2006 | First Round | Stainsby Hall v Sawley and Long Eaton Park | St Johns Road, Smalley | Results |
| 28 May 2006 | First Round | Staveley Welfare v Swarkestone | Lowgates, Staveley | Results |
| 28 May 2006 | First Round | Ticknall v Lullington Park | The Grange, Ticknall | Results |
| 28 May 2006 | First Round | Tutbury v Chesterfield Second XI | Tutbury Mill, Tutbury | Results |
| 28 May 2006 | First Round | Wirksworth and Middleton v Denby Second XI | The Recreation Ground, Wirksworth | Results |
| 04 Jun 2006 | First Round | Ambergate v Shipley Hall | The Hurt Arms Ground, Ambergate | Results |
| 04 Jun 2006 | First Round | Sandiacre Town Second XI v Clay Cross | Longmoor Lane, Sandiacre | Results |
| 11 Jun 2006 | First Round | Rolleston v West Hallam White Rose | Dovecliff Road, Rolleston-on-Dove | Results |
| 18 Jun 2006 | Second Round | Barton-under-Needwood v Riddings | Holland Park Sports Club Ground, Barton-under-Needwood | Results |
| 18 Jun 2006 | Second Round | Brailsford and Ednaston v Denby Second XI | Pools Head Lane, Brailsford | Results |
| 18 Jun 2006 | Second Round | Duffield v Swarkestone | Eyes Meadow, Duffield | Results |
| 18 Jun 2006 | First Round | Elvaston v Sandiacre Town Second XI | Stable Drive, Elvaston | Results |
| 18 Jun 2006 | Second Round | Matlock v Shipley Hall | Causeway Lane, Matlock | Results |
| 18 Jun 2006 | Second Round | Nutbrook v Rolls Royce | Nutbrook Sports Ground, West Hallam | Results |
| 18 Jun 2006 | Second Round | Rolleston v Lullington Park | Dovecliff Road, Rolleston-on-Dove | Results |
| 18 Jun 2006 | Second Round | Sawley and Long Eaton Park v Chesterfield Second XI | West Park, Long Eaton | Results |
| 09 Jul 2006 | Quarter-Final | Barton-under-Needwood v Denby Second XI | Holland Park Sports Club Ground, Barton-under-Needwood | Results |
| 09 Jul 2006 | Quarter-Final | Lullington Park v Elvaston | Lullington Park, Lullington | Results |
| 09 Jul 2006 | Quarter-Final | Matlock v Nutbrook | Causeway Lane, Matlock | Results |
| 09 Jul 2006 | Quarter-Final | Sawley and Long Eaton Park v Swarkestone | West Park, Long Eaton | Results |
| 30 Jul 2006 | Semi-Final | Lullington Park v Barton-under-Needwood | Lullington Park, Lullington | Results |
| 30 Jul 2006 | Semi-Final | Nutbrook v Swarkestone | Nutbrook Sports Ground, West Hallam | Results |
| 28 Aug 2006 | Final | Lullington Park v Swarkestone | The Maryfield, Ripley | Results |
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