| 21 May 2009 | First Round | Nomansland v Cadnam | Village Green, Nomansland | Results |
| 14 May 2009 | First Round | Paultons B v Swan Green | Whitemoor Lane, Ower | Results |
| 18 May 2009 | First Round | Langley Manor v Old Tauntonians and Romsey Academy | Knellers Lane, Totton | Results |
| 26 May 2009 | First Round | Michelmersh and Timsbury v Mottisfont | Mannyngham Way, Timsbury | Results |
| 21 May 2009 | First Round | Bramshaw v Broughton | Bramshaw Cricket Club Ground, Roundhills | Results |
| 26 May 2009 | First Round | Redlynch and Hale v Trojans | Redlynch Playing Field, Redlynch | Results |
| 14 May 2009 | First Round | Totton and Eling v Paultons A | Southern Gardens, Totton | Results |
| 14 May 2009 | First Round | Hampshire Collegiate School v Old Tauntonians and Romsey A | Hampshire Collegiate School, Embley Park | Results |
| 26 May 2009 | Second Round | Old Tauntonians and Romsey Academy v East Tytherley | Hunts Farm Playing Fields, Timsbury | Results |
| 26 May 2009 | Second Round | Highfield v Calmore Sports | Hardmoor Playing Fields, Southampton | Results |
| 26 May 2009 | Second Round | Ashurst v Whiteparish | Bolton's Bench, Lyndhurst | Results |
| 08 Jun 2009 | Second Round | Trojans v Old Tauntonians and Romsey B | The Trojans Club, Eastleigh | Results |
| 26 May 2009 | Second Round | Paultons A v Old Tauntonians and Romsey A | Whitemoor Lane, Ower | Results |
| 26 May 2009 | Second Round | Cadnam v Ampfield | Lambs Corner, Southampton | Results |
| 01 Jun 2009 | Second Round | Michelmersh and Timsbury v Swan Green | Mannyngham Way, Timsbury | Results |
| 26 May 2009 | Second Round | Bramshaw v Wellow and Plaitford | Bramshaw Cricket Club Ground, Roundhills | Results |
| 23 Jun 2009 | Quarter-Final | Swan Green v Old Tauntonians and Romsey A | Swan Green, Lyndhurst | Results |
| 26 Jun 2009 | Quarter-Final | Ashurst v Bramshaw | Bolton's Bench, Lyndhurst | Results |
| 23 Jun 2009 | Quarter-Final | Highfield v Cadnam | Hardmoor Playing Fields, Southampton | Results |
| 23 Jun 2009 | Quarter-Final | Trojans v East Tytherley | The Trojans Club, Eastleigh | Results |
| 14 Jul 2009 | Semi-Final | Highfield v Old Tauntonians and Romsey A | Hardmoor Playing Fields, Southampton | Results |
| 14 Jul 2009 | Semi-Final | Trojans v Bramshaw | The Trojans Club, Eastleigh | Results |
| 04 Aug 2009 | Final | Old Tauntonians and Romsey A v Trojans | Romsey Sports Centre, Romsey | Results |
| 11 Jun 2009 | Plate First Round | Hampshire Collegiate School v Broughton | Hampshire Collegiate School, Embley Park | Results |
| 11 Jun 2009 | Plate First Round | Totton and Eling v Old Tauntonians and Romsey B | Southern Gardens, Totton | Results |
| 11 Jun 2009 | Plate First Round | Redlynch and Hale v Langley Manor | Redlynch Playing Field, Redlynch | Results |
| 11 Jun 2009 | Plate First Round | Paultons B v Paultons A | Whitemoor Lane, Ower | Results |
| 11 Jun 2009 | Plate First Round | Calmore Sports v Nomansland | Loperwood Park, Calmore | Results |
| 11 Jun 2009 | Plate First Round | Michelmersh and Timsbury v Wellow and Plaitford | Mannyngham Way, Timsbury | Results |
| 11 Jun 2009 | Plate First Round | Old Tauntonians and Romsey Academy v Ampfield | Hunts Farm Playing Fields, Timsbury | Results |
| 11 Jun 2009 | Plate First Round | Whiteparish v Mottisfont | Memorial Ground, Whiteparish | Results |
| 23 Jun 2009 | Plate Quarter-Final | Old Tauntonians and Romsey B v Mottisfont | Romsey Sports Centre, Romsey | Results |
| 23 Jun 2009 | Plate Quarter-Final | Calmore Sports v Ampfield | Loperwood Park, Calmore | Results |
| 23 Jun 2009 | Plate Quarter-Final | Hampshire Collegiate School v Paultons A | Hampshire Collegiate School, Embley Park | Results |
| 23 Jun 2009 | Plate Quarter-Final | Redlynch and Hale v Wellow and Plaitford | Redlynch Playing Field, Redlynch | Results |
| 23 Jul 2009 | Plate Semi-Final | Old Tauntonians and Romsey B v Paultons A | Romsey Sports Centre, Romsey | Results |
| 14 Jul 2009 | Plate Semi-Final | Calmore Sports v Redlynch and Hale | Loperwood Park, Calmore | Results |
| 05 Aug 2009 | Plate Final | Paultons A v Redlynch and Hale | Redlynch Playing Field, Redlynch | Results |
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