| Played on 27th October 2008 | ||||
| Home | Away | |||
| 6 | Horstead Keynes | v | F.V.C. A | 1 |
| Cricketers | v | BYE | ||
| 2 | Royal Oak | v | Piltdown Man | 5 |
| 5 | Fountain | v | Tally Ho | 2 |
| 4 | Kings Head | v | Brewers B | 3 |
| 4 | White Horse | v | Watermill | 3 |
| 1 | United Services | v | Bar Nun | 6 |
| Ardingly RBL | v | BYE | ||
| Next Round to be played on Monday 9th February 2009 |
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| 4 | Cricketers | v | Bar Nun | 3 |
| 0 | White Horse | v | Piltdown Man | 7 |
| 3 | Horstead Keynes | v | Kings Head | 4 |
| 5 | Fountain | v | Ardingly RBL | 2 |
| Semi-Final to be played on Monday 30th March 2009 |
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| 3 | Fountain | v | Piltdown Man | 4 |
| 4 | Kings Head | v | Cricketers | 3 |
| Final played on 21st May 2009 | ||||
| 3 | Kings Head | v | Piltdown Man | 4 |