| 14 Jun 2009 | First Round | Alton v Hartley Wintney | Jubilee Playing Fields, Alton | Results |
| 14 Jun 2009 | First Round | Burridge v Gosport Borough | Burridge Sports Ground, Burridge | Results |
| 14 Jun 2009 | First Round | Easton and Martyr Worthy v Hook and Newnham Basics | The David Roth Cricket Ground, Easton | Results |
| 14 Jun 2009 | First Round | Fareham and Crofton v Purbrook | Bath Lane Recreation Ground, Fareham | Results |
| 07 Jun 2009 | First Round | Havant v Totton and Eling | Havant Park, Havant | Results |
| 14 Jun 2009 | First Round | Hursley Park v Old Tauntonians and Romsey | The Quarters, Hursley | Results |
| 14 Jun 2009 | First Round | New Milton v Tichborne Park | Fernhill Sports Ground, New Milton | Results |
| 14 Jun 2009 | First Round | Paultons v Bashley (Rydal) | Whitemoor Lane, Ower | Results |
| 14 Jun 2009 | First Round | Portsmouth v United Services Portsmouth | Hilsea, Portsmouth | Results |
| 14 Jun 2009 | First Round | Sarisbury Athletic v Ventnor | The Hollow, Sarisbury | Results |
| 14 Jun 2009 | First Round | South Wilts v St Cross Symondians | Bemerton Sports Ground, Salisbury | Results |
| 14 Jun 2009 | First Round | Trojans v Portsmouth and Southsea | The Trojans Club, Eastleigh | Results |
| 21 Jun 2009 | First Round | Andover v Rowledge | Batchelors Barn Road, Andover | Results |
| 21 Jun 2009 | First Round | Fair Oak v Hambledon | Lapstone Park, Fair Oak | Results |
| 30 Jun 2009 | Second Round | Alton v South Wilts | Jubilee Playing Fields, Alton | Results |
| 30 Jun 2009 | Second Round | Hook and Newnham Basics v Andover | King George V Playing Field, Hook | Results |
| 30 Jun 2009 | Second Round | Bashley (Rydal) v New Milton | Bashley Road, Bashley | Results |
| 30 Jun 2009 | Second Round | Bournemouth v Burridge | Chapel Gate, Bournemouth | Results |
| 30 Jun 2009 | Second Round | Hursley Park v Lymington | The Quarters, Hursley | Results |
| 30 Jun 2009 | Second Round | Portsmouth and Southsea v Hambledon | St James Hospital Ground, Milton | Results |
| 30 Jun 2009 | Second Round | Totton and Eling v Portsmouth and Southsea | Southern Gardens, Totton | Results |
| 30 Jun 2009 | Second Round | Ventnor v Fareham and Crofton | Steephill Road, Ventnor | Results |
| 12 Jul 2009 | Quarter-Final | Portsmouth v Alton | St Helen's Field, Southsea | Results |
| 12 Jul 2009 | Quarter-Final | Portsmouth and Southsea v Andover | St James Hospital Ground, Milton | Results |
| 12 Jul 2009 | Quarter-Final | Ventnor v Bournemouth | Steephill Road, Ventnor | Results |
| 19 Jul 2009 | Quarter-Final | Bashley (Rydal) v Lymington | Bashley Road, Bashley | Results |
| 26 Jul 2009 | Semi-Final | Lymington v Portsmouth | The Sports Ground, Lymington | Results |
| 26 Jul 2009 | Semi-Final | Ventnor v Andover | Steephill Road, Ventnor | Results |
| 19 Aug 2009 | Final | Lymington v Ventnor | Utilita Bowl, Southampton | Results |
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