| 16 Jun 2009 | First Round | Earls Barton v East Haddon | The Grange Sportsfield, Earls Barton | Results |
| 16 Jun 2009 | First Round | Finedon Dolben v Wollaston | Dolben Cricket Ground, Finedon | Results |
| 16 Jun 2009 | First Round | Great Houghton v Brixworth | Great Houghton Playing Field, Great Houghton | Results |
| 16 Jun 2009 | First Round | Great Oakley v Geddington | Lewin Road, Great Oakley | Results |
| 16 Jun 2009 | First Round | Horton House v Overstone Park | Denton Road, Horton | Results |
| 16 Jun 2009 | First Round | Irthlingborough Town v Burton Latimer | Windmill Road, Irthlingborough | Results |
| 16 Jun 2009 | First Round | Mears Ashby v Cogenhoe | Mears Ashby Playing Field, Mears Ashby | Results |
| 16 Jun 2009 | First Round | Obelisk v Kislingbury Temperance | The Obelisk Centre, Northampton | Results |
| 16 Jun 2009 | First Round | Old Northamptonians v Ashby Timken | Billing Road, Northampton | Results |
| 16 Jun 2009 | First Round | Raunds Town v Loddington and Mawsley | The Carter Hill Ground, Raunds | Results |
| 16 Jun 2009 | First Round | Rothwell Town v Rushton | Desborough Road, Rothwell | Results |
| 16 Jun 2009 | First Round | Rushden Town v Isham | Town Ground, Rushden | Results |
| 16 Jun 2009 | First Round | Stewarts and Lloyds Corby v Wellingborough Town | Stewart and Lloyds Sports Club Ground, Corby | Results |
| 16 Jun 2009 | First Round | Stony Stratford v Northampton Saints | Ostlers Lane, Stony Stratford | Results |
| 16 Jun 2009 | First Round | Weekley and Warkton v Oundle Town | Boughton Park, Weekley | Results |
| 16 Jun 2009 | First Round | Wellingborough Old Grammarians v Wellingborough Indians | The Memorial Sports Ground, Wellingborough | Results |
| 30 Jun 2009 | Second Round | Brixworth v Cogenhoe | Northampton Road, Brixworth | Results |
| 30 Jun 2009 | Second Round | Kislingbury Temperance v Old Northamptonians | Kislingbury Playing Fields, Kislingbury | Results |
| 30 Jun 2009 | Second Round | Oundle Town v Finedon Dolben | Milton Road, Oundle | Results |
| 30 Jun 2009 | Second Round | Overstone Park v Earls Barton | Overstone Road, Sywell | Results |
| 30 Jun 2009 | Second Round | Rothwell Town v Loddington and Mawsley | Desborough Road, Rothwell | Results |
| 30 Jun 2009 | Second Round | Rushden Town v Burton Latimer | Town Ground, Rushden | Results |
| 30 Jun 2009 | Second Round | Wellingborough Old Grammarians v Northampton Saints | The Memorial Sports Ground, Wellingborough | Results |
| 30 Jun 2009 | Second Round | Wellingborough Town v Geddington | Redwell Road, Wellingborough | Results |
| 14 Jul 2009 | Quarter-Final | Loddington and Mawsley v Finedon Dolben | Loddington Playing Field, Loddington | Results |
| 14 Jul 2009 | Quarter-Final | Northampton Saints v Burton Latimer | Birchfield Road East, Northampton | Results |
| 14 Jul 2009 | Quarter-Final | Old Northamptonians v Brixworth | Billing Road, Northampton | Results |
| 14 Jul 2009 | Quarter-Final | Wellingborough Town v Overstone Park | Redwell Road, Wellingborough | Results |
| 26 Jul 2009 | Semi-Final | not known v not known | not arranged | Results |
| 26 Jul 2009 | Semi-Final | not known v not known | not arranged | Results |
| 26 Jul 2009 | Final | not known v not known | not arranged | Results |
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