| 01 Jun 2008 | First Round | Darley Abbey v Swanwick Hall | Riverside Meadow, Darley Abbey | Results |
| 01 Jun 2008 | First Round | Elvaston Second XI v Alfreton Second XI | Stable Drive, Elvaston | Results |
| 01 Jun 2008 | First Round | Ilkeston Rutland Second XI v Burton | Rutland Recreation Ground, Ilkeston | Results |
| 01 Jun 2008 | First Round | Lullington Park Third XI v Riddings | Lullington Park Pitch 2, Lullington | Results |
| 01 Jun 2008 | First Round | Rolleston Second XI v Darley Abbey Second XI | Dovecliff Road, Rolleston-on-Dove | Results |
| 01 Jun 2008 | First Round | Swarkestone Second XI v Littleover Centurions | Barrow Turn, Swarkestone | Results |
| 01 Jun 2008 | First Round | Ticknall Second XI v Ashbourne | The Grange, Ticknall | Results |
| 01 Jun 2008 | First Round | Walton-on-Trent v Clowne Town | Station Lane, Walton-on-Trent | Results |
| 08 Jun 2008 | First Round | Sawley and Long Eaton Park Second XI v Little Eaton | King Street, Long Eaton | Results |
| 08 Jun 2008 | First Round | South Wingfield Second XI v Marehay Second XI | Holme Lane, South Wingfield | Results |
| 08 Jun 2008 | First Round | West Hallam White Rose v Melbourne Town | Cock Orchard, West Hallam | Results |
| 08 Jun 2008 | First Round | Breadsall v Hilton | Brookside Road, Breadsall | Results |
| 08 Jun 2008 | First Round | Cromford Meadows v Clifton Second XI | Cromford Meadows, Cromford | Results |
| 08 Jun 2008 | First Round | Langley Mill United v Heanor Town | Station Road, Langley Mill | Results |
| 08 Jun 2008 | First Round | Ockbrook and Borrowash Third XI v Morton Colliery | Victoria Avenue Pitch 2, Ockbrook | Results |
| 08 Jun 2008 | First Round | Riddings Second XI v Lullington Park Second XI | Riddings Park, Riddings | Results |
| 15 Jun 2008 | Second Round | Alfreton Second XI v Little Eaton | Alfreton Park, Alfreton | Results |
| 15 Jun 2008 | Second Round | Cromford Meadows v Marehay Second XI | Cromford Meadows, Cromford | Results |
| 15 Jun 2008 | Second Round | Darley Abbey v Morton Colliery | Riverside Meadow, Darley Abbey | Results |
| 15 Jun 2008 | Second Round | Ilkeston Rutland Second XI v West Hallam White Rose | Rutland Recreation Ground, Ilkeston | Results |
| 15 Jun 2008 | Second Round | Langley Mill United v Rolleston Second XI | Station Road, Langley Mill | Results |
| 15 Jun 2008 | Second Round | Riddings v Hilton | Riddings Park, Riddings | Results |
| 15 Jun 2008 | Second Round | Swarkestone Second XI v Walton-on-Trent | Barrow Turn, Swarkestone | Results |
| 15 Jun 2008 | Second Round | Ticknall Second XI v Lullington Park Second XI | The Grange, Ticknall | Results |
| 29 Jun 2008 | Quarter-Final | Langley Mill United v Alfreton Second XI | Station Road, Langley Mill | Results |
| 29 Jun 2008 | Quarter-Final | Marehay Second XI v West Hallam White Rose | The Maryfield, Ripley | Results |
| 29 Jun 2008 | Quarter-Final | Walton-on-Trent v Morton Colliery | Station Lane, Walton-on-Trent | Results |
| 13 Jul 2008 | Quarter-Final | Hilton v Lullington Park Second XI | Marston Lane End, Hilton | Results |
| 20 Jul 2008 | Semi-Final | Hilton v Marehay Second XI | Marston Lane End, Hilton | Results |
| 20 Jul 2008 | Semi-Final | Walton-on-Trent v Langley Mill United | Station Lane, Walton-on-Trent | Results |
| 24 Aug 2008 | Final | Hilton v Langley Mill United | Alfreton Park, Alfreton | Results |
| 29 Jun 2008 | First Round | Hilton v Lullington Park Second XI | Marston Lane End, Hilton | Results |
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