| 05 Jun 2016 | First Round | Ryde v Waterlooville | Harding Shute, Ryde | Results |
| 12 Jun 2016 | First Round | Alton v Trojans | Jubilee Playing Fields, Alton | Results |
| 12 Jun 2016 | First Round | Bashley (Rydal) v Basingstoke and North Hants | Bashley Road, Bashley | Results |
| 12 Jun 2016 | First Round | Bournemouth v Old Tauntonians and Romsey | Chapel Gate, Bournemouth | Results |
| 12 Jun 2016 | First Round | Burridge v Sparsholt | Burridge Sports Ground, Burridge | Results |
| 12 Jun 2016 | First Round | Calmore Sports v Sarisbury Athletic | Loperwood Park, Calmore | Results |
| 12 Jun 2016 | First Round | Hampshire Cricket Academy v Tichborne Park | Utilita Bowl (Nursery), Southampton | Results |
| 12 Jun 2016 | First Round | Hursley Park v Gosport Borough | The Quarters, Hursley | Results |
| 12 Jun 2016 | First Round | Langley Manor v Lymington | Knellers Lane, Totton | Results |
| 12 Jun 2016 | First Round | Paultons v Andover | Whitemoor Lane, Ower | Results |
| 12 Jun 2016 | First Round | Rowledge v Liphook and Ripsley | Rowledge Recreation Ground, Rowledge | Results |
| 12 Jun 2016 | First Round | South Wilts v Fawley | Bemerton Sports Ground, Salisbury | Results |
| 12 Jun 2016 | First Round | Totton and Eling v Hook and Newnham Basics | Southern Gardens, Totton | Results |
| 12 Jun 2016 | First Round | Ventnor v St Cross Symondians | Newclose County Cricket Ground, Newport | Results |
| 19 Jun 2016 | First Round | Fair Oak v Portsmouth | Lapstone Park, Fair Oak | Results |
| 03 Jul 2016 | Second Round | Alton v Andover | Jubilee Playing Fields, Alton | Results |
| 03 Jul 2016 | Second Round | Bashley (Rydal) v Hook and Newnham Basics | Bashley Road, Bashley | Results |
| 03 Jul 2016 | Second Round | Hursley Park v Old Tauntonians and Romsey | The Quarters, Hursley | Results |
| 03 Jul 2016 | Second Round | Liphook and Ripsley v Hampshire Cricket Academy | Liphook Recreation Ground, Liphook | Results |
| 03 Jul 2016 | Second Round | Lymington v Portsmouth | The Sports Ground, Lymington | Results |
| 03 Jul 2016 | Second Round | New Milton v Havant | Fernhill Sports Ground, New Milton | Results |
| 03 Jul 2016 | Second Round | Ventnor v Sarisbury Athletic | Newclose County Cricket Ground, Newport | Results |
| 03 Jul 2016 | Second Round | Waterlooville v South Wilts | Rowlands Avenue Recreation Ground, Waterlooville | Results |
| 24 Jul 2016 | Quarter-Final | South Wilts v Hook and Newnham Basics | Bemerton Sports Ground, Salisbury | Results |
| 24 Jul 2016 | Quarter-Final | Old Tauntonians and Romsey v Havant | Romsey Sports Centre, Romsey | Results |
| 24 Jul 2016 | Quarter-Final | Alton v Lymington | Jubilee Playing Fields, Alton | Results |
| 24 Jul 2016 | Quarter-Final | Liphook and Ripsley v Sarisbury Athletic | Liphook Recreation Ground, Liphook | Results |
| 14 Aug 2016 | Semi-Final | South Wilts v Sarisbury Athletic | Bemerton Sports Ground, Salisbury | Results |
| 14 Aug 2016 | Semi-Final | Lymington v Havant | The Sports Ground, Lymington | Results |
| 04 Sep 2016 | Final | Havant v Sarisbury Athletic | Utilita Bowl (Nursery), Southampton | Results |
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