28/10/2008, League week 2
| Southern Bell | 7 | 5 | Chatham X |
| Good Intent A | 10 | 2 | Nags Head A |
| Chatham Spitfires | 10 | 2 | Three Sisters |
| Chatham Z | 9 | 3 | Good Intent LB |
| Westcourt A | 7 | 5 | Rileys Jolly Boys |
| Cricketers | 7 | 5 | George |
| Chatham A | 8 | 4 | Chatham Luvvies |
| Rileys A | 7 | 5 | Bridgewardens |
| Monarch A | 3 | 9 | Walnut Tree |
| Concorde | 7 | 5 | Rose (Rochester) |
| White Lion B | 5 | 7 | Monarch B |
| Rileys Rejects | 9 | 3 | Allhallows Golf |
| Nags Head Social | 5 | 7 | White Lion A |
| Fox | 6 | 6 | Parkwood A |
| Parkwood B | 9 | 3 | Bell |
| Rose A | 8 | 4 | Chatham Outsiders |
| Dewdrop B | 7 | 5 | Rileys CS |
| Canopus A | 2 | 10 | Dewdrop A |
| General at Sea B | 7 | 5 | Rose B |
| Canterbury Tales | 3 | 9 | Westcourt S |
| Westcourt D | 4 | 8 | Cannon |
| Rileys X | 7 | 5 | General at Sea A |
| Hastings Arms | 10 | 2 | Canopus B |
| The Ship | 5 | 7 | Gillingham Labour |
| Beacon Court | 4 | 8 | Westcourt C |