| Reserve Division Two | |||
| 25/08/1999 | Skelmanthorpe | 5 - 4 | Lockwood |
| 01/09/1999 | New Mill 94 | 0 - 1 | Skelmanthorpe |
| 04/09/1999 | Scholes | 1 - 2 | Skelmanthorpe |
| 11/09/1999 | Skelmanthorpe | 1 - 0 | Wooldale Wanderers |
| 18/09/1999 | Diggle A | 4 - 4 | Skelmanthorpe |
| 25/09/1999 | Skelmanthorpe | 4 - 1 | Honley 'A' |
| 02/10/1999 | Marsden | 3 - 2 | Skelmanthorpe |
| 09/10/1999 | Skelmanthorpe | 4 - 1 | Uppermill 'A' |
| 16/10/1999 | Honley 'A' | 0 - 6 | Skelmanthorpe |
| 23/10/1999 | Netherton | 1 - 1 | Skelmanthorpe |
| 30/10/1999 | Sovereign Sports | 3 - 4 | Skelmanthorpe |
| 06/11/1999 | Skelmanthorpe | 7 - 1 | Scissett |
| 13/11/1999 | Skelmanthorpe | 5 - 2 | Kirkheaton Rovers 'A' |
| FA Junior Cup Round Two | |||
| 20/11/1999 | Deanhousemuir | 1 - 8 | Skelmanthorpe |
| 27/11/1999 | Kirkheaton Rovers 'A' | 2 - 0 | Skelmanthorpe |
| 04/12/1999 | Skelmanthorpe | 4 - 0 | Sovereign Sports |
| Richardson Cup Round One | |||
| 08/01/2000 | Heywood Sports | 3 - 5 | Skelmanthorpe |
| FA Junior Cup Round Three Quarter Finals | |||
| 15/01/2000 | Slaithwaite Utd | 1 - 1 | Skelmanthorpe |
| 22/01/2000 | Lockwood | 1 - 2 | Skelmanthorpe |
| 29/01/2000 | Almondbury Utd 'A' | 2 - 3 | Skelmanthorpe |
| 05/02/2000 | Skelmanthorpe | 4 - 0 | Scholes |
| 12/02/2000 | Wooldale Wanderers | 2 - 4 | Skelmanthorpe |
| 12/02/2000 | Uppermill 'A' | 3 - 7 | Skelmanthorpe |
| Richardson Cup Round Two | |||
| 19/02/2000 | Skelmanthorpe | 5 - 2 | Shepley |
| FA Junior Cup Round Three Quarter Finals | |||
| 26/02/2000 | Skelmanthorpe | 2 - 0 | Slaithwaite Utd |
| 04/03/2000 | Skelmanthorpe | 5 - 0 | Netherton |
| Richardson Cup Round Three Quarter Final | |||
| 25/03/2000 | Skelmanthorpe | 2 - 1 | To Be Decided |
| 01/04/2000 | Scissett | 1 - 7 | Skelmanthorpe |
| FA Junior Cup Semi Final | |||
| 07/04/2000 | Skelmanthorpe | 1 - 3 | Almondbury Utd |
| Richardson Cup Semi Final | |||
| 11/04/2000 | Almondbury Utd | 2 - 0 | Skelmanthorpe |
| 15/04/2000 | Skelmanthorpe | 3 - 1 | Marsden |
| 18/04/2000 | Skelmanthorpe | 3 - 2 | New Mill 94 |
| 22/04/2000 | Skelmanthorpe | 4 - 3 | Diggle A |
| 27/04/2000 | Skelmanthorpe | 1 - 7 | Almondbury Utd 'A' |