| Division Four | |||
| 04/09/1999 | Hade Edge | 4 - 4 | G.P.O. Sports |
| 11/09/1999 | Netherthong | 1 - 0 | G.P.O. Sports |
| 18/09/1999 | G.P.O. Sports | 3 - 2 | Scapegoat Hill Utd |
| 25/09/1999 | Aimbry | 4 - 4 | G.P.O. Sports |
| 02/10/1999 | G.P.O. Sports | 3 - 0 | Upperthong SC |
| 09/10/1999 | The Stag FC | 4 - 2 | G.P.O. Sports |
| FA Challenge Cup Round One | |||
| 16/10/1999 | G.P.O. Sports | 1 - 2 | Lepton Highlanders |
| 23/10/1999 | Woodman | 1 - 2 | G.P.O. Sports |
| 30/10/1999 | Holmbridge | 2 - 1 | G.P.O. Sports |
| West Riding Challenge Trophy Round Two | |||
| 06/11/1999 | G.P.O. Sports | P - P | Cleckheaton Athletic |
| 20/11/1999 | Scapegoat Hill Utd | 1 - 3 | G.P.O. Sports |
| 27/11/1999 | G.P.O. Sports | 1 - 4 | Weavers |
| West Riding Challenge Trophy Round Three | |||
| 04/12/1999 | G.P.O. Sports | 0 - 2 | Whitkirk Wanderers |
| 18/12/1999 | G.P.O. Sports | 7 - 0 | Walkers Arms |
| Groom Cup Round One | |||
| 08/01/2000 | Hade Edge | 3 - 0 | G.P.O. Sports |
| 15/01/2000 | G.P.O. Sports | 4 - 2 | Aimbry |
| 22/01/2000 | G.P.O. Sports | 1 - 2 | Hade Edge |
| 29/01/2000 | G.P.O. Sports | 3 - 1 | Netherthong |
| 05/02/2000 | Upperthong SC | 0 - 2 | G.P.O. Sports |
| 19/02/2000 | Weavers | 4 - 3 | G.P.O. Sports |
| 26/02/2000 | G.P.O. Sports | 1 - 3 | The Stag FC |
| 04/03/2000 | G.P.O. Sports | 1 - 2 | Woodman |
| 11/03/2000 | Walkers Arms | 3 - 2 | G.P.O. Sports |
| 08/04/2000 | G.P.O. Sports | 0 - 2 | Holmbridge |