| 16 May 2010 | First Round | Clifton Second XI v West Hallam White Rose Second XI | Chapel Lane, Clifton | Results |
| 16 May 2010 | First Round | Codnor v Elvaston Third XI | Goose Lane, Codnor | Results |
| 16 May 2010 | First Round | Langley Mill United Second XI v Rosehill Methodists | Station Road, Langley Mill | Results |
| 16 May 2010 | First Round | Lullington Park Third XI v Barton-under-Needwood | Lullington Park Pitch 2, Lullington | Results |
| 16 May 2010 | First Round | Rolleston Second XI v Denby Third XI | Dovecliff Road, Rolleston-on-Dove | Results |
| 16 May 2010 | First Round | South Wingfield Second XI v Castle Donington Town | Holme Lane, South Wingfield | Results |
| 16 May 2010 | First Round | Staveley Welfare Second XI v Cutthorpe Second XI | Lowgates, Staveley | Results |
| 16 May 2010 | First Round | Swarkestone Second XI v Matlock Second XI | Barrow Turn, Swarkestone | Results |
| 16 May 2010 | First Round | Uttoxeter v Alfreton Third XI | Uttoxeter Racecourse, Uttoxeter | Results |
| 20 Jun 2010 | Second Round | Elvaston Third XI v Rolleston Second XI | Stable Drive, Elvaston | Results |
| 20 Jun 2010 | Second Round | Heanor Town Second XI v Spondon Third XI | Town Ground, Heanor | Results |
| 20 Jun 2010 | Second Round | Langley Mill United Second XI v Lullington Park Third XI | Station Road, Langley Mill | Results |
| 20 Jun 2010 | Second Round | Nutbrook Second XI v Staveley Welfare Second XI | Nutbrook Sports Ground, West Hallam | Results |
| 20 Jun 2010 | Second Round | Ockbrook and Borrowash Third XI v Derby Congregational Second XI | Victoria Avenue Pitch 2, Ockbrook | Results |
| 20 Jun 2010 | Second Round | Stanton Elks v Clifton Second XI | The Stute, Ilkeston | Results |
| 20 Jun 2010 | Second Round | Swarkestone Second XI v Uttoxeter | Barrow Turn, Swarkestone | Results |
| 20 Jun 2010 | Second Round | Trentside Second XI v South Wingfield Second XI | Faldo Close, Branston | Results |
| 04 Jul 2010 | Quarter-Final | Elvaston Third XI v Langley Mill United Second XI | Stable Drive, Elvaston | Results |
| 04 Jul 2010 | Quarter-Final | Nutbrook Second XI v Stanton Elks | Nutbrook Sports Ground, West Hallam | Results |
| 04 Jul 2010 | Quarter-Final | Spondon Third XI v Derby Congregational Second XI | Locko Road Pitch 2, Spondon | Results |
| 04 Jul 2010 | Quarter-Final | Trentside Second XI v Swarkestone Second XI | Faldo Close, Branston | Results |
| 18 Jul 2010 | Semi-Final | Derby Congregational Second XI v Trentside Second XI | Brayfield Road, Littleover | Results |
| 18 Jul 2010 | Semi-Final | Langley Mill United Second XI v Nutbrook Second XI | Station Road, Langley Mill | Results |
| 22 Aug 2010 | Final | Derby Congregational Second XI v Nutbrook Second XI | St Johns Road, Smalley | Results |
| 13 Jun 2010 | First Round | Langley Mill United v Lullington Park Third XI | Station Road, Langley Mill | Results |
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