| August |
| Sat 24/8/1991 | NCEL1 | Brodsworth Welfare |  | 2-3 |  | Pickering Town | |
| September |
| Sat 7/9/1991 | FAVEP | Pickering Town | | 4-0 |  | Seaton Delaval Seaton Terrace | |
| Sat 14/9/1991 | NCEL1 | York Railway Institute |  | 2-2 | | Pickering Town | |
| Sat 21/9/1991 | NCEL1 | Tadcaster Albion |  | 1-3 | | Pickering Town | |
| Sat 28/9/1991 | NCEL1 | Pickering Town | | 2-2 | | York Railway Institute | |
| October |
| Sat 5/10/1991 | FAVP | Chester-le-Street | | 2-1 | | Pickering Town | |
| Sat 12/10/1991 | NCEL1 | Hatfield Main |  | 1-2 | | Pickering Town | |
| Sat 19/10/1991 | NCEL1 | Pickering Town | | 5-1 |  | Stocksbridge Park Steels | |
| Sat 26/10/1991 | NCEL1 | Worsbrough Bridge Athletic |  | 2-2 | | Pickering Town | |
| November |
| Sat 2/11/1991 | NCEL1 | Pickering Town | | 2-1 |  | Yorkshire Amateur | |
| Sat 9/11/1991 | NRCC1 | Pickering Town | | 3-5 | | Tees Components | |
| Sat 16/11/1991 | LC2 | North Ferriby United |  | 3-0 | | Pickering Town | |
| Sat 23/11/1991 | NCEL1 | Parkgate |  | 3-1 | | Pickering Town | |
| Sat 30/11/1991 | NCEL1 | Pickering Town | | 2-3 |  | Bradley Rangers | |
| December |
| Sat 7/12/1991 | NCEL1 | Bradley Rangers | | 1-0 | | Pickering Town | |
| Sat 14/12/1991 | NCEL1 | Pickering Town | | 5-2 | | Brodsworth Welfare | |
| Sat 28/12/1991 | NCEL1 | Pickering Town | | 3-8 |  | Hall Road Rangers | |
| January |
| Sat 4/1/1992 | NCEL1 | Hallam |  | 3-4 | | Pickering Town | |
| Sat 11/1/1992 | NCEL1 | Pickering Town | | 3-1 | | Tadcaster Albion | |
| Sat 18/1/1992 | NCEL1 | Rossington Main |  | 1-0 | | Pickering Town | |
| Sat 25/1/1992 | NRSC2Q | Marske United | | 2-0 | | Pickering Town | |
| February |
| Sat 8/2/1992 | NCEL1 | Immingham Town |  | 1-3 | | Pickering Town | |
| Sat 15/2/1992 | NCEL1 | Pickering Town | | 4-4 | | Worsbrough Bridge Athletic | |
| Sat 22/2/1992 | NCEL1 | Yorkshire Amateur | | 0-3 | | Pickering Town | |
| Sat 29/2/1992 | NCEL1 | Pickering Town | | 5-0 | | Parkgate | |
| March |
| Sat 7/3/1992 | NCEL1 | Selby Town |  | 1-2 | | Pickering Town | |
| Sat 14/3/1992 | NCEL1 | Pickering Town | | 3-2 | | Rossington Main | |
| Sat 21/3/1992 | NCEL1 | Pickering Town | | 5-0 | | Selby Town | |
| Sat 28/3/1992 | NCEL1 | Pickering Town | | 0-2 | | Hallam | |
| April |
| Sat 4/4/1992 | NCEL1 | Pickering Town | | 8-0 | | Immingham Town | |
| Sat 11/4/1992 | NCEL1 | Pickering Town | | 5-0 | | Hatfield Main | |
| Sat 18/4/1992 | NCEL1 | Pickering Town | | 2-0 |  | Garforth Town | |
| Mon 20/4/1992 | NCEL1 | Hall Road Rangers | | 0-2 | | Pickering Town | |
| Sat 25/4/1992 | NCEL1 | Stocksbridge Park Steels | | 2-1 | | Pickering Town | |
| May |
| Sat 2/5/1992 | NCEL1 | Garforth Town | | 0-2 | | Pickering Town | |