| Saturday, 05 September 2009 14:00
|
| Mid Sussex Football League Division 9 | Cuckfield Rangers II | 6 | - | 3 | Wivelsfield Green II | |
| Saturday, 12 September 2009 14:00
|
| Mid Sussex Football League Division 9 | Handcross Village II | 1 | - | 2 | Cuckfield Rangers II | |
| Saturday, 19 September 2009 14:00
|
| Mid Sussex Football League Division 9 | Cuckfield Rangers II | 0 | - | 8 | United Services | |
| Saturday, 26 September 2009 14:00
|
| Mid Sussex Football League Division 9 | Copthorne III | 6 | - | 5 | Cuckfield Rangers II | |
| Saturday, 03 October 2009 13:30
|
| Tester Cup | Cuckfield Rangers II | 2 | - | 1 | East Grinstead Mavericks | |
| Saturday, 10 October 2009 14:00
|
| Mid Sussex Football League Division 9 | Cuckfield Rangers II | 1 | - | 1 | Plumpton Athletic II | |
| Saturday, 17 October 2009 13:30
|
| Parsons Challenge Cup | Fletching II | 0 | - | 2 | Cuckfield Rangers II | |
| Saturday, 24 October 2009 14:00
|
| Mid Sussex Football League Division 9 | Cuckfield Rangers II | 3 | - | 1 | Lindfield IV | |
| Saturday, 31 October 2009 14:00
|
| Mid Sussex Football League Division 9 | Cuckfield Rangers II | 6 | - | 1 | Framfield & Blackboys United II | |
| Saturday, 07 November 2009 14:00
|
| Mid Sussex Football League Division 9 | United Services | 2 | - | 3 | Cuckfield Rangers II | |
| Saturday, 14 November 2009 14:00
|
| Mid Sussex Football League Division 9 | Cuckfield Rangers II | | - | | Scaynes Hill II | |
| Saturday, 28 November 2009 14:00
|
| Mid Sussex Football League Division 9 | Maresfield Village IV | | - | | Cuckfield Rangers II | |
