| 30 Apr 2006 | Preliminary Round | Cromford Meadows v Sawley and Long Eaton Park Third XI | Cromford Meadows, Cromford | Results |
| 30 Apr 2006 | Preliminary Round | Darley Abbey Second XI v Denby Third XI | Riverside Meadow, Darley Abbey | Results |
| 30 Apr 2006 | Preliminary Round | Nutbrook Second XI v Kirk Langley | Nutbrook Sports Ground, West Hallam | Results |
| 28 May 2006 | First Round | Butterley United v Rolls Royce Second XI | Nottingham Road Recreation Ground, Ripley | Results |
| 28 May 2006 | First Round | Clay Cross Second XI v Winshill | Sharley Park, Clay Cross | Results |
| 28 May 2006 | First Round | Darley Abbey Second XI v Elvaston Third XI | Riverside Meadow, Darley Abbey | Results |
| 28 May 2006 | First Round | Duffield Second XI v Etwall Second XI | Eyes Meadow, Duffield | Results |
| 28 May 2006 | First Round | Heanor Town Second XI v Ambergate Second XI | Town Ground, Heanor | Results |
| 28 May 2006 | First Round | Lullington Park Third XI v Wirksworth and Middleton Second XI | Lullington Park, Lullington | Results |
| 28 May 2006 | First Round | Matlock Second XI v Littleover Centurions Second XI | Causeway Lane, Matlock | Results |
| 28 May 2006 | First Round | South Wingfield Second XI v Sawley and Long Eaton Park Third XI | Holme Lane, South Wingfield | Results |
| 28 May 2006 | First Round | Swarkestone Second XI v Codnor | Barrow Turn, Swarkestone | Results |
| 28 May 2006 | First Round | Trentside Second XI v Nutbrook Second XI | Faldo Close, Branston | Results |
| 28 May 2006 | First Round | Alfreton Second XI v Barton-under-Needwood Second XI | Alfreton Park, Alfreton | Results |
| 28 May 2006 | First Round | Belper Amateurs Second XI v Tutbury Second XI | The Packhorse Ground, Alderwasley | Results |
| 28 May 2006 | First Round | Brailsford and Ednaston Second XI v Sandiacre Town Third XI | Pools Head Lane, Brailsford | Results |
| 04 Jun 2006 | First Round | West Hallam White Rose Second XI v Wingerworth | Beech Lane, West Hallam | Results |
| 04 Jun 2006 | First Round | Whitmoor Rowing Club v Riddings Second XI | Deer Park, Wingerworth | Results |
| 18 Jun 2006 | Second Round | Belper Amateurs Second XI v Darley Abbey Second XI | The Packhorse Ground, Alderwasley | Results |
| 18 Jun 2006 | Second Round | Heanor Town Second XI v Littleover Centurions Second XI | Town Ground, Heanor | Results |
| 18 Jun 2006 | Second Round | Lullington Park Third XI v Brailsford and Ednaston Second XI | Lullington Park, Lullington | Results |
| 18 Jun 2006 | Second Round | Riddings Second XI v Alfreton Second XI | Riddings Park, Riddings | Results |
| 18 Jun 2006 | Second Round | Rolls Royce Second XI v Nutbrook Second XI | Rolls Royce Ground, Derby | Results |
| 18 Jun 2006 | Second Round | Rosehill Methodists v Wingerworth | Littleover Lane Cricket Ground, Littleover | Results |
| 18 Jun 2006 | Second Round | Swarkestone Second XI v Duffield Second XI | Barrow Turn, Swarkestone | Results |
| 18 Jun 2006 | Second Round | Winshill v Sawley and Long Eaton Park Third XI | Mill Hill Lane, Winshill | Results |
| 09 Jul 2006 | Quarter-Final | Lullington Park Third XI v Heanor Town Second XI | Lullington Park Pitch 2, Lullington | Results |
| 09 Jul 2006 | Quarter-Final | Nutbrook Second XI v Wingerworth | Nutbrook Sports Ground, West Hallam | Results |
| 09 Jul 2006 | Quarter-Final | Swarkestone Second XI v Darley Abbey Second XI | Barrow Turn, Swarkestone | Results |
| 09 Jul 2006 | Quarter-Final | Winshill v Riddings Second XI | Mill Hill Lane, Winshill | Results |
| 30 Jul 2006 | Semi-Final | Darley Abbey Second XI v Nutbrook Second XI | Riverside Meadow, Darley Abbey | Results |
| 30 Jul 2006 | Semi-Final | Winshill v Heanor Town Second XI | Mill Hill Lane, Winshill | Results |
| 20 Aug 2006 | Final | Heanor Town Second XI v Nutbrook Second XI | The Copper Yard, Denby Village | Results |
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