| Mick Boakes Trophy | Whitmore Cup | Howard Cup | Star and Garter | George Jenns |
| 1st Round | Quarter Finals | Semi Finals | Final |
| TBP by 13 Nov 08 | TBP by 12 Dec 08 | ||
| Limpsfield R.B.L. - 256 | Caterham Club | ||
| Merstham V.C. - 210 | Limpsfield R.B.L. | ||
| Marlpit Hill | |||
| Oxted R.B.L. | |||
| Purley Social Club | |||
| Westerham R.B.L. | |||
| Biggin Hill Squash | |||
| Caterham CIU Sports | |||
| 7 BYES | |||
| Biggin Hill Squash | |||
| Caterham CIU Sports | |||
| Caterham Club | |||
| Marlpit Hill | |||
| Oxted R.B.L. | |||
| Purley Social Club | |||
| Westerham R.B.L. |