21/10/2008, League week 1
| Nags Head A | 6 | 6 | Southern Bell |
| Rileys Teds | 9 | 3 | Good Intent A |
| Good Intent LB | 3 | 9 | Chatham Spitfires |
| Medway Queen | 3 | 9 | Chatham Z |
| Rileys Jolly Boys | 4 | 8 | Star Meadow |
| George | 6 | 6 | Westcourt A |
| Chatham Luvvies | 8 | 4 | Cricketers |
| Bridgewardens | 3 | 9 | Chatham A |
| Walnut Tree | 7 | 5 | Rileys A |
| Rose (Rochester) | 6 | 6 | Fox |
| Monarch B | 3 | 9 | Concorde |
| Allhallows Golf | 3 | 9 | Royal Marine |
| White Lion A | 2 | 10 | Rileys Rejects |
| Parkwood A | 7 | 5 | Nags Head Social |
| Bell | 5 | 7 | Canterbury Tales |
| Chatham Outsiders | 7 | 5 | Parkwood B |
| Rileys CS | 7 | 5 | Rose A |
| Dewdrop A | 5 | 7 | Dewdrop B |
| Rose B | 0 | 9 | Canopus A |
| Westcourt S | 6 | 6 | General at Sea B |
| Cannon | 11 | 1 | Beacon Court |
| General at Sea A | 8 | 4 | Westcourt D |
| Canopus B | 5 | 7 | Rileys X |
| Gillingham Labour | 10 | 2 | Hastings Arms |
| Rileys Z | 8 | 4 | The Ship |