| Division One | |||
| 07/09/2002 | Skelmanthorpe | 2 - 3 | Wooldale Wanderers |
| Sheffield Junior Challenge Cup Round One | |||
| 14/09/2002 | Wooldale Wanderers | P - P | Upperthong SC |
| 21/09/2002 | Wooldale Wanderers | 4 - 2 | Sovereign Sports |
| 28/09/2002 | Grange Moor | 3 - 2 | Wooldale Wanderers |
| 05/10/2002 | Wooldale Wanderers | 2 - 1 | Diggle |
| Sheffield Junior Challenge Cup Round Two | |||
| 12/10/2002 | Phoenix Allstars FC | 3 - 4 | Wooldale Wanderers |
| FA Challenge Cup Round One | |||
| 19/10/2002 | Wooldale Wanderers | 4 - 3 | Mount |
| 26/10/2002 | Wooldale Wanderers | 3 - 3 | Brackenhall Utd |
| 02/11/2002 | Britannia Sports | 2 - 3 | Wooldale Wanderers |
| Sheffield Junior Challenge Cup Round Three | |||
| 09/11/2002 | Wooldale Wanderers | 3 - 4 | Golden Plover |
| FA Challenge Cup Round Two | |||
| 16/11/2002 | Lockwood | 1 - 10 | Wooldale Wanderers |
| 23/11/2002 | Wooldale Wanderers | 3 - 1 | Heywood Sports |
| 30/11/2002 | Heywood Sports | 1 - 4 | Wooldale Wanderers |
| 07/12/2002 | Wooldale Wanderers | 4 - 4 | Britannia Sports |
| Barlow Cup Round Two | |||
| 14/12/2002 | Kirkheaton Rovers | 2 - 1 | Wooldale Wanderers |
| 28/12/2002 | Wooldale Wanderers | 7 - 1 | Skelmanthorpe |
| FA Challenge Cup Round Three | |||
| 18/01/2003 | Wooldale Wanderers | 2 - 0 | New Mill 94 |
| 25/01/2003 | Sovereign Sports | 0 - 0 | Wooldale Wanderers |
| 01/02/2003 | Wooldale Wanderers | 2 - 2 | Grange Moor |
| FA Challenge Cup Round Four Quarter Final | |||
| 15/02/2003 | Golcar Utd (WR) | 5 - 1 | Wooldale Wanderers |
| 22/02/2003 | Brackenhall Utd | 3 - 2 | Wooldale Wanderers |
| 01/03/2003 | Wooldale Wanderers | 0 - 0 | Kirkheaton Rovers |
| 08/03/2003 | Kirkheaton Rovers | 2 - 2 | Wooldale Wanderers |
| 15/03/2003 | Wooldale Wanderers | 3 - 2 | Slaithwaite Utd |
| 22/03/2003 | Slaithwaite Utd | 2 - 2 | Wooldale Wanderers |
| 29/03/2003 | Diggle | 3 - 0 | Wooldale Wanderers |
| 05/04/2003 | Shepley | 2 - 2 | Wooldale Wanderers |
| 12/04/2003 | Wooldale Wanderers | 0 - 2 | Shepley |
| 15/04/2003 | Wooldale Wanderers | 2 - 0 | Honley |
| 26/04/2003 | Honley | 5 - 1 | Wooldale Wanderers |