| 10 May 2008 | | Ashford Town Third XI v Wickham Park | Stacians Park Annex Ground, Ashford | Results |
| 10 May 2008 | | Catford Wanderers v Walmer | Catford Wanderers Sports and Social Club, Catford | Results |
| 10 May 2008 | | Gravesend v Upchurch | Bat and Ball Ground, Gravesend | Results |
| 10 May 2008 | | Holmesdale v Linden Park | Montreal Park, Sevenoaks | Results |
| 10 May 2008 | | HSBC v Minster (Sheppey) | HSBC Sports and Social Club, Beckenham | Results |
| 17 May 2008 | | Linden Park v Ashford Town Third XI | Higher Common Ground, Tunbridge Wells | Results |
| 17 May 2008 | | Minster (Sheppey) v Gravesend | Gilbert Hall, Minster | Results |
| 17 May 2008 | | Upchurch v Holmesdale | Holywell Meadow, Upchurch | Results |
| 17 May 2008 | | Walmer v HSBC | Hull Park Sports Club, Deal | Results |
| 17 May 2008 | | Wickham Park v Catford Wanderers | Wickham Park Sports Club Ground, West Wickham | Results |
| 24 May 2008 | | Ashford Town Third XI v Walmer | Stacians Park Annex Ground, Ashford | Results |
| 24 May 2008 | | Catford Wanderers v Minster (Sheppey) | Catford Wanderers Sports and Social Club, Catford | Results |
| 24 May 2008 | | Gravesend v Holmesdale | Bat and Ball Ground, Gravesend | Results |
| 24 May 2008 | | HSBC v Upchurch | HSBC Sports and Social Club, Beckenham | Results |
| 24 May 2008 | | Wickham Park v Linden Park | Wickham Park Sports Club Ground, West Wickham | Results |
| 31 May 2008 | | Holmesdale v HSBC | Montreal Park, Sevenoaks | Results |
| 31 May 2008 | | Linden Park v Gravesend | Higher Common Ground, Tunbridge Wells | Results |
| 31 May 2008 | | Minster (Sheppey) v Ashford Town Third XI | Gilbert Hall, Minster | Results |
| 31 May 2008 | | Upchurch v Catford Wanderers | Holywell Meadow, Upchurch | Results |
| 31 May 2008 | | Walmer v Wickham Park | Hull Park Sports Club, Deal | Results |
| 07 Jun 2008 | | Ashford Town Third XI v Holmesdale | Stacians Park Annex Ground, Ashford | Results |
| 07 Jun 2008 | | Catford Wanderers v Gravesend | Catford Wanderers Sports and Social Club, Catford | Results |
| 07 Jun 2008 | | HSBC v Linden Park | HSBC Sports and Social Club, Beckenham | Results |
| 07 Jun 2008 | | Walmer v Minster (Sheppey) | Hull Park Sports Club, Deal | Results |
| 07 Jun 2008 | | Wickham Park v Upchurch | Wickham Park Sports Club Ground, West Wickham | Results |
| 14 Jun 2008 | | Gravesend v HSBC | Bat and Ball Ground, Gravesend | Results |
| 14 Jun 2008 | | Holmesdale v Catford Wanderers | Montreal Park, Sevenoaks | Results |
| 14 Jun 2008 | | Linden Park v Walmer | Higher Common Ground, Tunbridge Wells | Results |
| 14 Jun 2008 | | Minster (Sheppey) v Wickham Park | Gilbert Hall, Minster | Results |
| 14 Jun 2008 | | Upchurch v Ashford Town Third XI | Holywell Meadow, Upchurch | Results |
| 21 Jun 2008 | | Catford Wanderers v Ashford Town Third XI | Catford Wanderers Sports and Social Club, Catford | Results |
| 21 Jun 2008 | | Gravesend v Walmer | Bat and Ball Ground, Gravesend | Results |
| 21 Jun 2008 | | Holmesdale v Minster (Sheppey) | Montreal Park, Sevenoaks | Results |
| 21 Jun 2008 | | HSBC v Wickham Park | HSBC Sports and Social Club, Beckenham | Results |
| 21 Jun 2008 | | Linden Park v Upchurch | Higher Common Ground, Tunbridge Wells | Results |
| 28 Jun 2008 | | Ashford Town Third XI v Gravesend | Stacians Park Annex Ground, Ashford | Results |
| 28 Jun 2008 | | Catford Wanderers v HSBC | Catford Wanderers Sports and Social Club, Catford | Results |
| 28 Jun 2008 | | Minster (Sheppey) v Linden Park | Gilbert Hall, Minster | Results |
| 28 Jun 2008 | | Walmer v Upchurch | Hull Park Sports Club, Deal | Results |
| 28 Jun 2008 | | Wickham Park v Holmesdale | Wickham Park Sports Club Ground, West Wickham | Results |
| 05 Jul 2008 | | Gravesend v Wickham Park | Bat and Ball Ground, Gravesend | Results |
| 05 Jul 2008 | | Holmesdale v Walmer | Montreal Park, Sevenoaks | Results |
| 05 Jul 2008 | | HSBC v Ashford Town Third XI | HSBC Sports and Social Club, Beckenham | Results |
| 05 Jul 2008 | | Linden Park v Catford Wanderers | Higher Common Ground, Tunbridge Wells | Results |
| 05 Jul 2008 | | Upchurch v Minster (Sheppey) | Holywell Meadow, Upchurch | Results |
| 12 Jul 2008 | | Linden Park v Holmesdale | Higher Common Ground, Tunbridge Wells | Results |
| 12 Jul 2008 | | Minster (Sheppey) v HSBC | Gilbert Hall, Minster | Results |
| 12 Jul 2008 | | Upchurch v Gravesend | Holywell Meadow, Upchurch | Results |
| 12 Jul 2008 | | Walmer v Catford Wanderers | Hull Park Sports Club, Deal | Results |
| 12 Jul 2008 | | Wickham Park v Ashford Town Third XI | Wickham Park Sports Club Ground, West Wickham | Results |
| 19 Jul 2008 | | Ashford Town Third XI v Linden Park | Stacians Park Annex Ground, Ashford | Results |
| 19 Jul 2008 | | Catford Wanderers v Wickham Park | Catford Wanderers Sports and Social Club, Catford | Results |
| 19 Jul 2008 | | Gravesend v Minster (Sheppey) | Bat and Ball Ground, Gravesend | Results |
| 19 Jul 2008 | | Holmesdale v Upchurch | Montreal Park, Sevenoaks | Results |
| 19 Jul 2008 | | HSBC v Walmer | HSBC Sports and Social Club, Beckenham | Results |
| 26 Jul 2008 | | Holmesdale v Gravesend | Montreal Park, Sevenoaks | Results |
| 26 Jul 2008 | | Linden Park v Wickham Park | Higher Common Ground, Tunbridge Wells | Results |
| 26 Jul 2008 | | Minster (Sheppey) v Catford Wanderers | Gilbert Hall, Minster | Results |
| 26 Jul 2008 | | Upchurch v HSBC | Holywell Meadow, Upchurch | Results |
| 26 Jul 2008 | | Walmer v Ashford Town Third XI | Hull Park Sports Club, Deal | Results |
| 02 Aug 2008 | | Ashford Town Third XI v Minster (Sheppey) | Stacians Park Annex Ground, Ashford | Results |
| 02 Aug 2008 | | Catford Wanderers v Upchurch | Catford Wanderers Sports and Social Club, Catford | Results |
| 02 Aug 2008 | | Gravesend v Linden Park | Bat and Ball Ground, Gravesend | Results |
| 02 Aug 2008 | | HSBC v Holmesdale | HSBC Sports and Social Club, Beckenham | Results |
| 02 Aug 2008 | | Wickham Park v Walmer | Wickham Park Sports Club Ground, West Wickham | Results |
| 09 Aug 2008 | | Gravesend v Catford Wanderers | Bat and Ball Ground, Gravesend | Results |
| 09 Aug 2008 | | Holmesdale v Ashford Town Third XI | Montreal Park, Sevenoaks | Results |
| 09 Aug 2008 | | Linden Park v HSBC | Higher Common Ground, Tunbridge Wells | Results |
| 09 Aug 2008 | | Minster (Sheppey) v Walmer | Gilbert Hall, Minster | Results |
| 09 Aug 2008 | | Upchurch v Wickham Park | Holywell Meadow, Upchurch | Results |
| 16 Aug 2008 | | Ashford Town Third XI v Upchurch | Stacians Park Annex Ground, Ashford | Results |
| 16 Aug 2008 | | Catford Wanderers v Holmesdale | Catford Wanderers Sports and Social Club, Catford | Results |
| 16 Aug 2008 | | HSBC v Gravesend | HSBC Sports and Social Club, Beckenham | Results |
| 16 Aug 2008 | | Walmer v Linden Park | Hull Park Sports Club, Deal | Results |
| 16 Aug 2008 | | Wickham Park v Minster (Sheppey) | Wickham Park Sports Club Ground, West Wickham | Results |
| 23 Aug 2008 | | Ashford Town Third XI v Catford Wanderers | Stacians Park Annex Ground, Ashford | Results |
| 23 Aug 2008 | | Minster (Sheppey) v Holmesdale | Gilbert Hall, Minster | Results |
| 23 Aug 2008 | | Upchurch v Linden Park | Holywell Meadow, Upchurch | Results |
| 23 Aug 2008 | | Walmer v Gravesend | Hull Park Sports Club, Deal | Results |
| 23 Aug 2008 | | Wickham Park v HSBC | Wickham Park Sports Club Ground, West Wickham | Results |
| 30 Aug 2008 | | Gravesend v Ashford Town Third XI | Bat and Ball Ground, Gravesend | Results |
| 30 Aug 2008 | | Holmesdale v Wickham Park | Montreal Park, Sevenoaks | Results |
| 30 Aug 2008 | | HSBC v Catford Wanderers | HSBC Sports and Social Club, Beckenham | Results |
| 30 Aug 2008 | | Linden Park v Minster (Sheppey) | Higher Common Ground, Tunbridge Wells | Results |
| 30 Aug 2008 | | Upchurch v Walmer | Holywell Meadow, Upchurch | Results |
| 06 Sep 2008 | | Ashford Town Third XI v HSBC | Stacians Park Annex Ground, Ashford | Results |
| 06 Sep 2008 | | Catford Wanderers v Linden Park | Catford Wanderers Sports and Social Club, Catford | Results |
| 06 Sep 2008 | | Minster (Sheppey) v Upchurch | Gilbert Hall, Minster | Results |
| 06 Sep 2008 | | Walmer v Holmesdale | Hull Park Sports Club, Deal | Results |
| 06 Sep 2008 | | Wickham Park v Gravesend | Wickham Park Sports Club Ground, West Wickham | Results |
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