| 2022-07-30 15:00:0030/07/22 | Bishop Auckland v Pickering Town | 6 - 0 | Division 1 | 2022-23 | Heritage Park | | 304 |
| Wayne Whitfield (5) Craig Gott (23 pen) James Risborough (43, 65) Dane Burlace (54) Louis Johnson (79) |
| 2022-08-02 19:45:0002/08/22 | Newcastle Benfield v Pickering Town | 2 - 1 | Division 1 | 2022-23 | Sam Smith's Park | | 175 |
| Eddie Thomas (16) Cameron Gascoigne (57) |
| Bobby Rye (8), Jamie Thornton missed pen (56) |
| 2022-08-06 15:00:1506/08/22 | Heaton Stannington v Pickering Town | 1 - 0 | | 2022-23 | Grounsell Park | FA CupExtra Preliminary Round | 233 |
| Louis Anderson (12) |
| 2022-08-09 19:45:0009/08/22 | Pickering Town v Whickham | 0 - 2 | Division 1 | 2022-23 | Mill Lane | | 118 |
| Nathan Greenwood (17) Scott Robson (76) |
| 2022-08-13 15:00:0013/08/22 | West Allotment Celtic v Pickering Town | 7 - 1 | Division 1 | 2022-23 | East Palmersville Sports Pavilion | | 75 |
| Callum Larmouth (6, 7) Mechack Kanda (16, 73) Guy Bates (56, 82) Michael Baxter (53) |
| Bobby Rye (22) |
| 2022-08-16 19:45:0016/08/22 | Pickering Town v Tow Law Town | 2 - 1 | Division 1 | 2022-23 | Mill Lane | | 136 |
| Wayne Brooksby (14) Jamie Thornton (51) |
| Ethan Bewley (45) |
| 2022-08-20 15:00:0020/08/22 | Redcar Athletic v Pickering Town | 15:00:003:00 pm | Division 1 | 2022-23 | Green Lane | | |
| 2022-08-23 19:45:0023/08/22 | Pickering Town v Newton Aycliffe | 19:45:007:45 pm | Division 1 | 2022-23 | Mill Lane | | |
| 2022-08-27 15:00:0227/08/22 | Redcar Town v Pickering Town | 15:00:023:00 pm | | 2022-23 | The Vibrant Stadium | FA VaseFirst Round Qualifying | |
| 2022-08-31 19:45:0031/08/22 | Heaton Stannington v Pickering Town | 19:45:007:45 pm | Division 1 | 2022-23 | Grounsell Park | | |
| 2022-09-03 15:00:0003/09/22 | Whitley Bay v Pickering Town | 15:00:003:00 pm | Division 1 | 2022-23 | Hillheads Park | | |
| 2022-09-06 19:45:0006/09/22 | Pickering Town v Thornaby | 19:45:007:45 pm | Division 1 | 2022-23 | Mill Lane | | |
| 2022-09-10 15:00:0010/09/22 | Carlisle City v Pickering Town | 15:00:003:00 pm | Division 1 | 2022-23 | The Three Rivers Health & Safety Consultancy Stadium | | |
| 2022-09-17 15:00:0017/09/22 | Pickering Town v Penrith | 15:00:003:00 pm | Division 1 | 2022-23 | Mill Lane | | |
| 2022-10-01 15:00:0001/10/22 | Seaham Red Star v Pickering Town | 15:00:003:00 pm | Division 1 | 2022-23 | Independent Utility Advise Arena | | |
| 2022-10-04 19:45:0004/10/22 | Pickering Town v Northallerton Town | 19:45:007:45 pm | Division 1 | 2022-23 | Mill Lane | | |
| 2022-10-08 15:00:0008/10/22 | Pickering Town v Redcar Athletic | 15:00:003:00 pm | Division 1 | 2022-23 | Mill Lane | | |
| 2022-10-15 15:00:0015/10/22 | Crook Town v Pickering Town | 15:00:003:00 pm | Division 1 | 2022-23 | The Sir Tom Cowie Millfield | | |
| 2022-10-22 15:00:0022/10/22 | Pickering Town v Sunderland RCA | 15:00:003:00 pm | Division 1 | 2022-23 | Mill Lane | | |
| 2022-10-29 15:00:0029/10/22 | Pickering Town v Guisborough Town | 15:00:003:00 pm | Division 1 | 2022-23 | Mill Lane | | |
| 2022-11-05 15:00:0005/11/22 | West Auckland Town v Pickering Town | 15:00:003:00 pm | Division 1 | 2022-23 | Wanted Stadium | | |
| 2022-11-12 15:00:0012/11/22 | Pickering Town v Newcastle Benfield | 15:00:003:00 pm | Division 1 | 2022-23 | Mill Lane | | |
| 2022-11-19 15:00:0019/11/22 | Whickham v Pickering Town | 15:00:003:00 pm | Division 1 | 2022-23 | Glebe Sports Ground | | |
| 2022-11-26 15:00:0026/11/22 | Tow Law Town v Pickering Town | 15:00:003:00 pm | Division 1 | 2022-23 | Ironworks Road | | |
| 2022-12-03 15:00:0003/12/22 | Ashington AFC v Pickering Town | 15:00:003:00 pm | Division 1 | 2022-23 | Woodhorn Lane | | |
| 2022-12-10 15:00:0010/12/22 | Newton Aycliffe v Pickering Town | 15:00:003:00 pm | Division 1 | 2022-23 | Newton Aycliffe Sports Club | | |
| 2022-12-17 15:00:0017/12/22 | Pickering Town v Heaton Stannington | 15:00:003:00 pm | Division 1 | 2022-23 | Mill Lane | | |
| 2023-01-07 15:00:0007/01/23 | Thornaby v Pickering Town | 15:00:003:00 pm | Division 1 | 2022-23 | Teesdale Park | | |
| 2023-01-14 15:00:0014/01/23 | Pickering Town v Bishop Auckland | 15:00:003:00 pm | Division 1 | 2022-23 | Mill Lane | | |
| 2023-01-21 15:00:0021/01/23 | Northallerton Town v Pickering Town | 15:00:003:00 pm | Division 1 | 2022-23 | The Calvert Stadium | | |
| 2023-01-28 15:00:0028/01/23 | Pickering Town v West Allotment Celtic | 15:00:003:00 pm | Division 1 | 2022-23 | Mill Lane | | |
| 2023-02-04 15:00:0004/02/23 | Pickering Town v Ashington AFC | 15:00:003:00 pm | Division 1 | 2022-23 | Mill Lane | | |
| 2023-02-11 15:00:0011/02/23 | Pickering Town v Whitley Bay | 15:00:003:00 pm | Division 1 | 2022-23 | Mill Lane | | |
| 2023-02-18 15:00:0018/02/23 | Pickering Town v Carlisle City | 15:00:003:00 pm | Division 1 | 2022-23 | Mill Lane | | |
| 2023-02-25 15:00:0025/02/23 | Penrith v Pickering Town | 15:00:003:00 pm | Division 1 | 2022-23 | The Frenchfield Stadium | | |
| 2023-03-11 15:00:0011/03/23 | Pickering Town v Seaham Red Star | 15:00:003:00 pm | Division 1 | 2022-23 | Mill Lane | | |
| 2023-03-25 15:00:0025/03/23 | Pickering Town v Crook Town | 15:00:003:00 pm | Division 1 | 2022-23 | Mill Lane | | |
| 2023-04-08 15:00:0008/04/23 | Sunderland RCA v Pickering Town | 15:00:003:00 pm | Division 1 | 2022-23 | Sunderland LGV Park | | |
| 2023-04-15 15:00:0015/04/23 | Guisborough Town v Pickering Town | 15:00:003:00 pm | Division 1 | 2022-23 | King George V Ground | | |
| 2023-04-22 15:00:0022/04/23 | Pickering Town v West Auckland Town | 15:00:003:00 pm | Division 1 | 2022-23 | Mill Lane | | |
