| Mick Boakes Trophy | Whitmore Cup | Howard Cup | Pop Roberts | George Jenns |
| 1st Round | Quarter Finals | Semi Finals | Final |
| TBP by 12 Dec 08 | |||
| Westerham R.B.L. A - 244 | |||
| Oxted R.B.L. B - 166 | |||
| Caterham CIU Sports B | |||
| Caterham CIU Sports A | |||
| Marlpit Hill A | |||
| Biggin Hill Squash A | |||
| Westerham R.B.L. B - 145 | |||
|
Caterham Club A - 251 |
|||
| Caterham CIU Sports C | |||
| Marlpit Hill B | |||
| Caterham Club B | |||
| Caterham Club C | |||
| Oxted R.B.L. D - 237 | |||
| Westerham R.B.L. C - 137 | |||
| 1 BYE | |||
| Biggin Hill Squash B |