| Division Two | |||
| 25/08/1999 | Grange Moor | 5 - 1 | Sovereign Sports |
| 01/09/1999 | Sovereign Sports | 5 - 1 | Lepton Highlanders |
| 04/09/1999 | Hepworth Utd | 1 - 4 | Sovereign Sports |
| 11/09/1999 | Diggle | 2 - 3 | Sovereign Sports |
| 18/09/1999 | Sovereign Sports | 3 - 1 | Berry Brow Lib |
| 25/09/1999 | Mount | 0 - 2 | Sovereign Sports |
| 02/10/1999 | Sovereign Sports | 3 - 1 | Shelley |
| 09/10/1999 | Lockwood | 0 - 3 | Sovereign Sports |
| FA Challenge Cup Round One | |||
| 16/10/1999 | Sovereign Sports | 3 - 1 | Grange Moor |
| 23/10/1999 | Sovereign Sports | 4 - 0 | Meltham Athletic |
| 30/10/1999 | Lindley Liberal | 2 - 3 | Sovereign Sports |
| West Riding Challenge Trophy Round Two | |||
| 06/11/1999 | Pool Reserves | 2 - 4 | Sovereign Sports |
| FA Challenge Cup Round Two | |||
| 20/11/1999 | Little John | 3 - 2 | Sovereign Sports |
| 27/11/1999 | Sovereign Sports | 4 - 1 | Scholes |
| West Riding Challenge Trophy Round Three | |||
| 18/12/1999 | Sovereign Sports | 5 - 0 | Armley Athletic Res |
| Barlow Cup Round Two | |||
| 08/01/2000 | Shelley | 0 - 7 | Sovereign Sports |
| West Riding Challenge Trophy Round Four | |||
| 15/01/2000 | Hunsworth | 1 - 2 | Sovereign Sports |
| 22/01/2000 | Sovereign Sports | 1 - 0 | Grange Moor |
| Barlow Cup Round Three Quarter Final | |||
| 12/02/2000 | Kirkburton | 1 - 2 | Sovereign Sports |
| 19/02/2000 | Sovereign Sports | 1 - 3 | Slaithwaite Utd |
| 26/02/2000 | Scholes | 2 - 3 | Sovereign Sports |
| 04/03/2000 | Shelley | 1 - 5 | Sovereign Sports |
| 11/03/2000 | Sovereign Sports | 4 - 1 | Lockwood |
| 18/03/2000 | Meltham Athletic | 0 - 1 | Sovereign Sports |
| 25/03/2000 | Sovereign Sports | 2 - 0 | Lindley Liberal |
| 01/04/2000 | Sovereign Sports | 2 - 3 | Scissett |
| 08/04/2000 | Sovereign Sports | 0 - 1 | Diggle |
| 11/04/2000 | Slaithwaite Utd | 1 - 0 | Sovereign Sports |
| 15/04/2000 | Berry Brow Lib | 0 - 3 | Sovereign Sports |
| 18/04/2000 | Scissett | 5 - 4 | Sovereign Sports |
| Barlow Cup Semi Final | |||
| 24/04/2000 | Sovereign Sports | P - P | Honley |
| 27/04/2000 | Sovereign Sports | 0 - 2 | Mount |
| 29/04/2000 | Sovereign Sports | 3 - 1 | Hepworth Utd |
| 04/05/2000 | Lepton Highlanders | 0 - 5 | Sovereign Sports |