| 10 May 2009 | Group C | Alvaston and Boulton v Sandiacre Town | Raynesway, Alvaston | Results |
| 10 May 2009 | Group A | Caythorpe v Alfreton | Caythorpe Road, Caythorpe | Results |
| 10 May 2009 | Group A | Ilkeston Rutland v Chesterfield | Rutland Recreation Ground, Ilkeston | Results |
| 10 May 2009 | Group D | Kimberley Institute v Aston-on-Trent | Private Ground, Kimberley | Results |
| 10 May 2009 | Group B | Lullington Park v Ockbrook and Borrowash | Lullington Park, Lullington | Results |
| 10 May 2009 | Group C | Mansfield Hosiery Mills v Rolls Royce | The Fieldings, Sutton-in-Ashfield | Results |
| 10 May 2009 | Group D | Quarndon v Spondon | The Common, Quarndon | Results |
| 10 May 2009 | Group B | Wollaton v Dunstall | Main Road, Wollaton | Results |
| 07 Jun 2009 | Group C | Alvaston and Boulton v Mansfield Hosiery Mills | Raynesway, Alvaston | Results |
| 07 Jun 2009 | Group A | Ilkeston Rutland v Caythorpe | Rutland Recreation Ground, Ilkeston | Results |
| 07 Jun 2009 | Group B | Lullington Park v Wollaton | Lullington Park, Lullington | Results |
| 07 Jun 2009 | Group B | Ockbrook and Borrowash v Dunstall | Victoria Avenue, Ockbrook | Results |
| 07 Jun 2009 | Group D | Quarndon v Kimberley Institute | The Common, Quarndon | Results |
| 07 Jun 2009 | Group C | Sandiacre Town v Rolls Royce | Longmoor Lane, Sandiacre | Results |
| 07 Jun 2009 | Group D | Spondon v Aston-on-Trent | Locko Road, Spondon | Results |
| 14 Jun 2009 | Group A | Chesterfield v Alfreton | Queen's Park, Chesterfield | Results |
| 28 Jun 2009 | Group A | Alfreton v Ilkeston Rutland | Alfreton Park, Alfreton | Results |
| 28 Jun 2009 | Group D | Aston-on-Trent v Quarndon | Shardlow Road, Aston-on-Trent | Results |
| 28 Jun 2009 | Group A | Caythorpe v Chesterfield | Caythorpe Road, Caythorpe | Results |
| 28 Jun 2009 | Group B | Dunstall v Lullington Park | Deer Park, Dunstall | Results |
| 28 Jun 2009 | Group D | Kimberley Institute v Spondon | Private Ground, Kimberley | Results |
| 28 Jun 2009 | Group C | Mansfield Hosiery Mills v Sandiacre Town | The Fieldings, Sutton-in-Ashfield | Results |
| 28 Jun 2009 | Group C | Rolls Royce v Alvaston and Boulton | Rolls Royce Ground, Derby | Results |
| 28 Jun 2009 | Group B | Wollaton v Ockbrook and Borrowash | Main Road, Wollaton | Results |
| 02 Aug 2009 | Quarter-Final | Chesterfield v Rolls Royce | Queen's Park, Chesterfield | Results |
| 02 Aug 2009 | Quarter-Final | Kimberley Institute v Lullington Park | Private Ground, Kimberley | Results |
| 02 Aug 2009 | Quarter-Final | Ockbrook and Borrowash v Spondon | Victoria Avenue, Ockbrook | Results |
| 02 Aug 2009 | Quarter-Final | Sandiacre Town v Caythorpe | Longmoor Lane, Sandiacre | Results |
| 09 Aug 2009 | Semi-Final | Lullington Park v Chesterfield | Lullington Park, Lullington | Results |
| 16 Aug 2009 | Semi-Final | Caythorpe v Spondon | Caythorpe Road, Caythorpe | Results |
| 06 Sep 2009 | Final | Chesterfield v Caythorpe | Queen's Park, Chesterfield | Results |
| 19 Jul 2009 | Quarter-Final | Kimberley Institute v Lullington Park | Private Ground, Kimberley | Results |
| 26 Jul 2009 | Quarter-Final | Kimberley Institute v Lullington Park | Private Ground, Kimberley | Results |
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