| Date | Home | Away | Result | Scorers |
| 06/09/08 | Chinley Juniors | Droylsden Juniors B | P | |
| 13/09/08 | Juno United B | Chinley Juniors | 2-0 | |
| 20/09/08 | Chinley Juniors | FC Blue Star Satellites | 5-1 |
T Daley, J Howell (2) O Bradley (2) |
| 27/09/08 | High Lane Juniors | Chinley Juniors | 0-1 |
Tom Daley |
| 06/10/08 | Chinley Juniors | Hale United B | 0-2 | |
| 11/10/08 | Torpedo Juniors | Chinley Juniors | 0-4 |
O Bradley (2) T Daley C Kitchen |
| 18/10/08 | Chinley Juniors | Hollingworth Juniors B | P | |
| 25/10/08 | Bramhall North B | Chinley Juniors | P | |
| 01/11/08 | Chinley Juniors | Didsbury Junior Blacks | 0-1 | |
| 08/11/08 | Droylsden Juniors B | Chinley Juniors | 2-0 | |
| 15/11/08 | Chinley Juniors | Juno United | ||
| 22/11/08 | FC Blue Star Satellites | Chinley Juniors | ||
| 29/11/08 | Chinley Juniors | High Lane Juniors B | ||
| 06/12/08 | Hale United B | Chinley Juniors | ||
| 13/12/08 | Chinley Juniors | Torpedo Grove | ||
| CHRISTMAS & NEW YEAR | ||||
| 10/01/09 | Hollingworth Juniors B | Chinley Juniors | ||
| 17/01/09 | Chinley Juniors | Bramhall North B | ||
| 24/01/09 | Didsbury Junior Blacks | Chinley Juniors | ||
| 31/01/09 | Juno United B | Chinley Juniors | ||
| 07/02/09 | Chinley Juniors | Droylsden Juniors B | ||
| 14/02/09 | High Lane Juniors B | Chinley Juniors | ||
| 21/02/09 | Chinley Juniors | FC Blue Star Satellites | ||
| 28/02/09 | Chinley Juniors | Hale United B | ||
| 07/03/09 | Torpedo Grove | Chinley Juniors | ||
| 14/03/09 | Chinley Juniors | Hollingworth Juniors B | ||
| 21/03/09 | Bramhall North B | Chinley Juniors | ||
| 28/03/09 | Chinley Juniors | Didsbury Junior Blacks | ||