| 10 May 2009 | First Round | Elvaston Second XI v Ticknall Second XI | Stable Drive, Elvaston | Results |
| 10 May 2009 | First Round | Littleover Centurions v Ilkeston Rutland Second XI | King George V Fields, Littleover | Results |
| 10 May 2009 | First Round | Lullington Park Third XI v Langley Mill United | Lullington Park Pitch 2, Lullington | Results |
| 10 May 2009 | First Round | Riddings v Alvaston and Boulton Second XI | Riddings Park, Riddings | Results |
| 10 May 2009 | First Round | Sawley and Long Eaton Park Second XI v Clifton Second XI | King Street, Long Eaton | Results |
| 10 May 2009 | First Round | Swarkestone Second XI v Alfreton Second XI | Barrow Turn, Swarkestone | Results |
| 10 May 2009 | First Round | Walton-on-Trent v Cromford Meadows | Station Lane, Walton-on-Trent | Results |
| 10 May 2009 | First Round | Wirksworth and Middleton v Rolleston Second XI | The Recreation Ground, Wirksworth | Results |
| 10 May 2009 | First Round | Barton-under-Needwood v Allestree | Holland Park Sports Club Ground, Barton-under-Needwood | Results |
| 10 May 2009 | First Round | Belper Amateurs v Dunstall Second XI | The Packhorse Ground, Alderwasley | Results |
| 10 May 2009 | First Round | Burton v Hilton | The Town Ground, Burton-on-Trent | Results |
| 10 May 2009 | First Round | Darley Abbey v Marehay Second XI | Riverside Meadow, Darley Abbey | Results |
| 10 May 2009 | First Round | Denby Third XI v Little Eaton | The Copper Yard Pitch 2, Denby Village | Results |
| 14 Jun 2009 | Second Round | Allestree v Morton Colliery | The Recreation Ground, Allestree | Results |
| 14 Jun 2009 | Second Round | Belper Amateurs v Wirksworth and Middleton | The Packhorse Ground, Alderwasley | Results |
| 14 Jun 2009 | Second Round | Darley Abbey v Swanwick Hall | Riverside Meadow, Darley Abbey | Results |
| 14 Jun 2009 | Second Round | Denby Third XI v Riddings | The Copper Yard Pitch 2, Denby Village | Results |
| 14 Jun 2009 | Second Round | Elvaston Second XI v Mickleover | Stable Drive, Elvaston | Results |
| 14 Jun 2009 | Second Round | Hilton v Sawley and Long Eaton Park Second XI | Marston Lane End, Hilton | Results |
| 14 Jun 2009 | Second Round | Swarkestone Second XI v Langley Mill United | Barrow Turn, Swarkestone | Results |
| 14 Jun 2009 | Second Round | Walton-on-Trent v Littleover Centurions | Station Lane, Walton-on-Trent | Results |
| 28 Jun 2009 | Quarter-Final | Allestree v Darley Abbey | The Recreation Ground, Allestree | Results |
| 28 Jun 2009 | Quarter-Final | Elvaston Second XI v Riddings | Stable Drive, Elvaston | Results |
| 28 Jun 2009 | Quarter-Final | Hilton v Walton-on-Trent | Marston Lane End, Hilton | Results |
| 28 Jun 2009 | Quarter-Final | Wirksworth and Middleton v Langley Mill United | The Recreation Ground, Wirksworth | Results |
| 09 Aug 2009 | Semi-Final | Elvaston Second XI v Hilton | Stable Drive, Elvaston | Results |
| 09 Aug 2009 | Semi-Final | Langley Mill United v Darley Abbey | Station Road, Langley Mill | Results |
| 30 Aug 2009 | Final | Elvaston Second XI v Langley Mill United | Station Road, Mickleover | Results |
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