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| Monday 28th April 2008 | |||
| Combination 2 | |||
| AFC Aldermaston Res | 1 | 8 | Romsey Town Res |
| Tuesday 29th April 2008 | |||
| Final Sydenhams Wessex Combination Cup | |||
| Brading Town Res | 3 | 1 | VT FC Res |
| At Blackfield & Langley FC | |||
| Combination 1 | |||
| Lymington Town Res | 1 | 5 | Christchurch Res |
| Friday 2nd May 2008 | |||
| Isle of Wight Gold Cup | |||
| East Cowes Vics | 5 | 2 | Newport |
| At Cowes Sports | |||
| Portsmouth Senior Cup Final | |||
| Horndean Res | 2 | 2 | United Service Res |
| At Moneyfields | (Horndean won 6-5 on pens) | ||
| Saturday 3rd May 2008 | |||
| Final Sydenhams Wessex League Cup | |||
| Moneyfields | 0 | 1 | Wimborne Town |
| At Christchurch FC 3pm K O | |||
| Tuesday 6th May 2008 | |||
| Russell Cotes Cup Final | |||
| New Milton Town | Fleet Town | ||
| At New Milton FC | |||
| Friday 9th May 2008 | |||
| Isle of Wight Gold Cup Final | |||
| East Cowes Vics | Cowes Sports | ||
| At Cowes Sports | |||
| Saturday 10th May 2008 | |||
| Final Hampshire senior Cup | |||
| Basingstoke Town FC v Farnborough FC | |||
| At AFC Bournemouth | |||
| North Hants Senior Cup Final | |||
| Fleet Town | Tadley Calleva | ||
| At Fleet Town | |||
| At Brockenhurst FC | |||
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