| 1st. Round | 14 September 2008 | |||
| 2nd Round | 12 October 2008 | |||
| 3rd Round | 9 November 2008 | |||
| 4th Round | 14 December 2008 | |||
| 5th Round | 11 January 2009 | |||
| 6th Round | 15 February 2009 | |||
| 7th Round | 15 March 2009 | |||
| 8th Round | 12 April 2009 | |||
| FINALS | Under 11 | Sunday 19th April 2008 @ Blackfield & Langley FC | ||
| Under 12 | Sunday 19th April 2008 @ Blackfield & Langley FC | |||
| Under 13 | Sunday 5th April 2008 @ Fleet Town FC | |||
| Under 14 | Sunday 26th April 2008 @ Gosport Borough FC | |||
| Under 15 | Sunday 19th April 2008 @ Blackfield & Langley FC | |||
| Under 16 | Sunday 5th April 2008 @ Fleet Town FC | |||