| Date | Home | Away | Result |
| 14/09/08 | Marple Athletic | Chinley Juniors | 2-6 |
| 21/09/08 | Chinley Juniors | Didsbury Villa | 2-2 |
| 28/09/08 | Lostock Rangers | Chinley Juniors | 5-1 |
| 05/10/08 | Training at Buxworth | ||
| 12/10/08 | Chinley Juniors | Disley Juniors | |
| 19/10/08 | Cup Preliminary Round | ||
| 26/10/08 | No game | ||
| 02/11/08 | High Lane Juniors | Chinley Juniors | |
| 09/11/08 | Chinley Juniors | Timperley Villa | |
| 16/11/08 | Norbury Athletic | Chinley Juniors | |
| 23/11/08 | Cup First Round | ||
| 30/11/08 | Chinley Juniors | Marple Athletic | |
| 07/12/08 | Cheadle & Gatley | Chinley Juniors | |
| 14/12/08 | Chinley Juniors |
Lostock Rangers |
|
| CHRISTMAS & NEW YEAR | |||
| 04/01/09 | Didsbury Villa | Chinley Juniors | |
| 11/01/09 | Cup Second Round | ||
| 18/01/09 | Oldham Greenhil | Chinley Juniors | |
| 25/01/09 | Disley Juniors | Chinley Juniors | |
| 01/02/09 | Chinley Juniors | High Lane | |
| 08/02/09 | Timperley Villa | Chinley Juniors | |
| 17/02/09 | Chinley Juniors | Norbury | |
| tba | Chinley Juniors | Cheadle & Gatley | |
| tba | Chinley Juniors | Oldham Greenhil | |