| August | |||||||
| Sat 14/8/1999 | NCEL1 | Parkgate | | 1-2 | | Borrowash Victoria | |
| Wed 18/8/1999 | NCEL1 | Hall Road Rangers | | 2-0 | | Parkgate | |
| Sat 21/8/1999 | FACP | Parkgate | | 1-5 | | Eccleshill United | |
| Sat 28/8/1999 | NCEL1 | Parkgate | | 3-1 | | Louth United | |
| September | |||||||
| Sat 4/9/1999 | NCEL1 | Pontefract Collieries | | 2-1 | | Parkgate | |
| Sat 11/9/1999 | NCEL1 | Parkgate | | 1-2 | | Glapwell | |
| Sat 18/9/1999 | NCEL1 | Glapwell | | 2-2 | | Parkgate | |
| Tue 21/9/1999 | NCEL1 | Parkgate | | 3-1 | | Worsbrough Bridge Athletic | |
| Sat 25/9/1999 | FAV2Q | Evenwood Town | | 1-4 | | Parkgate | |
| October | |||||||
| Sat 2/10/1999 | NCEL1 | Mickleover Sports | | 0-3 | | Parkgate | |
| Sat 9/10/1999 | NCEL1 | Parkgate | | 1-5 | | Winterton Rangers | |
| Sat 16/10/1999 | NCEL1 | Hatfield Main | | 4-1 | | Parkgate | |
| Tue 19/10/1999 | LC1 | Yorkshire Amateur | | 2-1 | | Parkgate | |
| Sat 23/10/1999 | FAV1 | Abbey Hey | | 3-0 | | Parkgate | |
| Tue 26/10/1999 | PC2 | Parkgate | | 4-1 | | Maltby Main | |
| Sat 30/10/1999 | NCEL1 | Pickering Town | | 3-1 | | Parkgate | |
| November | |||||||
| Tue 2/11/1999 | WST1 | Parkgate | | 2-1 | | Rossington Main | |
| Sat 6/11/1999 | NCEL1 | Bridlington Town | | 1-3 | | Parkgate | |
| Tue 9/11/1999 | SHSC1 | Parkgate | | 4-2 | | Frecheville CA | |
| Sat 13/11/1999 | NCEL1 | Parkgate | | 2-0 | | Hatfield Main | |
| Sat 20/11/1999 | NCEL1 | Tadcaster Albion | | 2-7 | | Parkgate | |
| Tue 23/11/1999 | PC3 | Mickleover Sports | | 5-2 | | Parkgate | |
| Sat 27/11/1999 | NCEL1 | Parkgate | | 6-0 | | Tadcaster Albion | |
| December | |||||||
| Sat 4/12/1999 | NCEL1 | Worsbrough Bridge Athletic | | 0-2 | | Parkgate | |
| Tue 7/12/1999 | SHSC2 | Rossington Main | | 1-2 | | Parkgate | |
| Sat 11/12/1999 | NCEL1 | Parkgate | | 3-3 | | Hall Road Rangers | |
| Sat 18/12/1999 | NCEL1 | Louth United | | 2-0 | | Parkgate | |
| January | |||||||
| Sat 8/1/2000 | NCEL1 | Parkgate | | 2-2 | | Pontefract Collieries | |
| Sat 15/1/2000 | NCEL1 | Goole AFC | | 4-1 | | Parkgate | |
| Sat 22/1/2000 | NCEL1 | Parkgate | | 1-3 | | Yorkshire Amateur | |
| February | |||||||
| Sat 5/2/2000 | NCEL1 | Parkgate | | 3-4 | | Mickleover Sports | |
| Sat 12/2/2000 | NCEL1 | Winterton Rangers | | 1-2 | | Parkgate | |
| Sat 19/2/2000 | NCEL1 | Parkgate | | 4-1 | | Rossington Main | |
| Sat 26/2/2000 | NCEL1 | Rossington Main | | 4-0 | | Parkgate | |
| Tue 29/2/2000 | WST2 | Parkgate | | 1-3 | | Goole AFC | |
| March | |||||||
| Sat 4/3/2000 | NCEL1 | Parkgate | | 3-2 | | Pickering Town | |
| Tue 7/3/2000 | SHSC3 | Parkgate | | 1-3 | | Emley | |
| Sat 11/3/2000 | NCEL1 | Parkgate | | 2-2 | | Bridlington Town | |
| Sat 18/3/2000 | NCEL1 | Borrowash Victoria | | 3-0 | | Parkgate | |
| Sat 25/3/2000 | NCEL1 | Parkgate | | 0-1 | | Goole AFC | |
| April | |||||||
| Sat 1/4/2000 | NCEL1 | Yorkshire Amateur | | 0-0 | | Parkgate | |