| Division One | |||
| 06/09/2003 | Meltham Athletic | 9 - 1 | Wooldale Wanderers |
| Sheffield Junior Challenge Cup Round One | |||
| 13/09/2003 | Cartworth Moor | 1 - 3 | Wooldale Wanderers |
| 20/09/2003 | Slaithwaite Utd | 2 - 1 | Wooldale Wanderers |
| 27/09/2003 | Wooldale Wanderers | 1 - 1 | Skelmanthorpe |
| 04/10/2003 | Wooldale Wanderers | 1 - 1 | Grange Moor |
| Sheffield Junior Challenge Cup Round Two | |||
| 11/10/2003 | Dearne & District FC | 12 - 1 | Wooldale Wanderers |
| FA Challenge Cup Round One | |||
| 18/10/2003 | Wooldale Wanderers | 1 - 4 | Scholes |
| 25/10/2003 | Wooldale Wanderers | 3 - 3 | Honley |
| 01/11/2003 | Kirkburton | 3 - 0 | Wooldale Wanderers |
| Barlow Cup Round One | |||
| 08/11/2003 | Wooldale Wanderers | 1 - 2 | Storthes Hall |
| 15/11/2003 | Skelmanthorpe | 3 - 2 | Wooldale Wanderers |
| 22/11/2003 | Wooldale Wanderers | 4 - 5 | Diggle |
| 29/11/2003 | Heywood Sports | 7 - 4 | Wooldale Wanderers |
| 06/12/2003 | Wooldale Wanderers | 4 - 4 | Britannia Sports |
| 13/12/2003 | Kirkheaton Rovers | 3 - 0 | Wooldale Wanderers |
| 20/12/2003 | Grange Moor | 0 - 2 | Wooldale Wanderers |
| 03/01/2004 | Shepley | 3 - 0 | Wooldale Wanderers |
| 10/01/2004 | Wooldale Wanderers | 3 - 5 | Kirkheaton Rovers |
| 17/01/2004 | Wooldale Wanderers | 0 - 11 | Meltham Athletic |
| 24/01/2004 | Wooldale Wanderers | 0 - 5 | Slaithwaite Utd |
| 31/01/2004 | Britannia Sports | 2 - 2 | Wooldale Wanderers |
| 21/02/2004 | Honley | 4 - 3 | Wooldale Wanderers |
| 06/03/2004 | Diggle | 7 - 0 | Wooldale Wanderers |
| 13/03/2004 | Wooldale Wanderers | 0 - 6 | Heywood Sports |
| 27/03/2004 | Wooldale Wanderers | 4 - 2 | Kirkburton |
| 10/04/2004 | Wooldale Wanderers | 1 - 2 | Shepley |