| Mick Boakes Trophy | Whitmore Cup | Howard Cup | Star and Garter | Pop Roberts |
| 1st Round | Quarter Finals | Semi Finals | Final |
| TBP by 22 Jan 09 | TBP by 19 Feb 09 | TBC at Merstham V.C. | TBC at Merstham V.C. |
| Caterham CIU Sports | Westerham R.B.L. - Jimmy Williams | ||
| Merstham V.C. | Purley Social Club | ||
| Caterham CIU Sports or Merstham V.C. | |||
| Caterham Club | |||
| Biggin Hill Squash | |||
| Limpsfield R.B.L. | |||
| Marlpit Hill - Martin Hounslow | |||
| Oxted R.B.L. | |||
| 7 BYES | |||
| Biggin Hill Squash | |||
| Caterham Club | |||
| Limpsfield R.B.L. | |||
| Marlpit Hill | |||
| Oxted R.B.L. | |||
| Purley Social Club | |||
| Westerham R.B.L. |