| 08 Jun 2014 | First Round | Andover v Fawley | Batchelors Barn Road, Andover | Results |
| 08 Jun 2014 | First Round | Basingstoke and North Hants v Fair Oak | May's Bounty, Basingstoke | Results |
| 08 Jun 2014 | First Round | Hampshire Cricket Academy v Portsmouth and Southsea | Utilita Bowl (Nursery), Southampton | Results |
| 08 Jun 2014 | First Round | Hartley Wintney v New Milton | The Cricket Green, Hartley Wintney | Results |
| 08 Jun 2014 | First Round | Lymington v Totton and Eling | The Sports Ground, Lymington | Results |
| 08 Jun 2014 | First Round | Old Tauntonians and Romsey v Trojans | Romsey Sports Centre, Romsey | Results |
| 08 Jun 2014 | First Round | Sarisbury Athletic v Calmore Sports | The Hollow, Sarisbury | Results |
| 15 Jun 2014 | First Round | Havant v Hook and Newnham | Havant Park, Havant | Results |
| 15 Jun 2014 | First Round | Langley Manor v Bournemouth | Knellers Lane, Totton | Results |
| 15 Jun 2014 | First Round | Paultons v Portsmouth | Whitemoor Lane, Ower | Results |
| 15 Jun 2014 | First Round | St Cross Symondians v Alton | Green Jackets Ground, Winchester | Results |
| 15 Jun 2014 | First Round | Tichborne Park v Liphook and Ripsley | Tichborne Park, Tichborne | Results |
| 15 Jun 2014 | First Round | Waterlooville v Bashley (Rydal) | Rowlands Avenue Recreation Ground, Waterlooville | Results |
| 01 Jun 2014 | First Round | Ventnor v Sparsholt | Steephill Road, Ventnor | Results |
| 29 Jun 2014 | Second Round | Hampshire Cricket Academy v South Wilts | Utilita Bowl (Nursery), Southampton | Results |
| 29 Jun 2014 | Second Round | Paultons v Ventnor | Whitemoor Lane, Ower | Results |
| 29 Jun 2014 | Second Round | Tichborne Park v Burridge | Tichborne Park, Tichborne | Results |
| 06 Jul 2014 | Second Round | Andover v Hartley Wintney | Batchelors Barn Road, Andover | Results |
| 29 Jun 2014 | Second Round | Alton v Sarisbury Athletic | Jubilee Playing Fields, Alton | Results |
| 29 Jun 2014 | Second Round | Bashley (Rydal) v Lymington | Bashley Road, Bashley | Results |
| 29 Jun 2014 | Second Round | Bournemouth v Havant | Chapel Gate, Bournemouth | Results |
| 06 Jul 2014 | Second Round | Old Tauntonians and Romsey v Basingstoke and North Hants | Romsey Sports Centre, Romsey | Results |
| 13 Jul 2014 | Third Round | Lymington v Hartley Wintney | The Sports Ground, Lymington | Results |
| 13 Jul 2014 | Third Round | Sarisbury Athletic v Paultons | The Hollow, Sarisbury | Results |
| 13 Jul 2014 | Third Round | South Wilts v Basingstoke and North Hants | Bemerton Sports Ground, Salisbury | Results |
| 13 Jul 2014 | Third Round | Tichborne Park v Havant | Tichborne Park, Tichborne | Results |
| 03 Aug 2014 | Semi-Final | Sarisbury Athletic v South Wilts | The Hollow, Sarisbury | Results |
| 03 Aug 2014 | Semi-Final | Lymington v Havant | The Sports Ground, Lymington | Results |
| 15 Aug 2014 | Final | Lymington v South Wilts | Utilita Bowl, Southampton | Results |
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