| 2022-07-30 15:00:0030/07/22 | Billingham Synthonia v Esh Winning | 3 - 1 | Division 2 | 2022-23 | Stokesley Sports Club | | 84 |
| Danny Chapman (3, 43) Ash Lavan (38) |
| Jonathan Swift (33) |
| 2022-08-02 19:30:0002/08/22 | Horden CW v Esh Winning | 5 - 0 | Division 2 | 2022-23 | Horden Community Welfare Park | | 170 |
| Josh Home-Jackson (22) Jack Maskell (34) Liam Wright (72) Marc Ellison (77) David Doughty (87) |
| 2022-08-06 15:00:0006/08/22 | Esh Winning v Redcar Town | 2 - 1 | Division 2 | 2022-23 | The WindowsPlusRoofs Arena | | 61 |
| Corbyn Mitchell (15) Daniel Pringle (22) |
| Nico Weatherald (32) |
| 2022-08-09 19:30:0009/08/22 | Esh Winning v Willington | 1 - 0 | Division 2 | 2022-23 | The WindowsPlusRoofs Arena | | 130 |
| Thomas Olley (33) |
| 2022-08-13 15:00:0013/08/22 | Prudhoe YC Seniors v Esh Winning | 4 - 2 | Division 2 | 2022-23 | Essity Park | | 92 |
| Craig Fairley (46, 58, 70) Matthew Law (88) |
| Daniel Pringle (45) Owen Lister (56) |
| 2022-08-16 19:30:0016/08/22 | Boldon CA v Esh Winning | 1 - 1 | Division 2 | 2022-23 | Boldon Colliery Welfare Ground | | 48 |
| Luke Collins (69) |
| Connor Lowes (87) |
| 2022-08-20 15:00:0020/08/22 | Esh Winning v Blyth Town | 0 - 2 | Division 2 | 2022-23 | The WindowsPlusRoofs Arena | | 65 |
| Brandon Slater (17, 26) |
| 2022-08-23 19:30:0023/08/22 | Esh Winning v Bedlington Terriers | 0 - 0 | Division 2 | 2022-23 | The WindowsPlusRoofs Arena | | 83 |
| 2022-08-27 15:00:5727/08/22 | Newton Aycliffe v Esh Winning | 1 - 0 | | 2022-23 | Newton Aycliffe Sports Club | FA VaseFirst Round Qualifying | 162 |
| Liam Jarvie (64) |
| 2022-08-30 19:45:0030/08/22 | Sunderland West End v Esh Winning | 4 - 2 | Division 2 | 2022-23 | Ford Hub Sports Complex | | 60 |
| Owen Imeson (55), Samuel Peat (60), Ashley Davis 2 (70, 85) |
| Daniel Pringle (18), Connor Lowes (75) |
| 2022-09-03 15:00:0003/09/22 | Esh Winning v Newcastle University | 3 - 4 | Division 2 | 2022-23 | The WindowsPlusRoofs Arena | | 65 |
| Jonathan Swift (9, 45) Cobi Jones (30) |
| Charlie Ward (10) Jos Veitch (66, 68) Ryan Redford (61) |
| 2022-09-06 19:30:0006/09/22 | Esh Winning v Billingham Town | 0 - 4 | Division 2 | 2022-23 | The WindowsPlusRoofs Arena | | 70 |
| David Gordon (15 pen, 44 pen) Christopher Wallace (18) Jonathan Swift (26 og) |
| 2022-09-20 19:30:4920/09/22 | Dunston v Esh Winning | 4 - 2 | | 2022-23 | The UTS Stadium | Durham Challenge CupFirst Round | 94 |
| Willaim Jenkins (49) Michael Fowler (68) Sado Djalo (83) Liam Thear (85) |
| Willian Alves Olimpio (54) Lee McMahon (90 pen) |
| 2022-09-24 15:00:0024/09/22 | Esh Winning v Jarrow | 1 - 0 | Division 2 | 2022-23 | The WindowsPlusRoofs Arena | | 114 |
| Andrew Taylor (26) |
| 2022-10-01 15:00:0001/10/22 | Esh Winning v Ryton & Crawcrook Albion | 1 - 2 | Division 2 | 2022-23 | The WindowsPlusRoofs Arena | | 61 |
| Cobi Jones (30) |
| Jay Roper (6 pen) Joe Thompson (32) |
| 2022-10-08 15:00:0008/10/22 | Birtley Town v Esh Winning | 15:00:003:00 pm | Division 2 | 2022-23 | The Arrowmark Home Improvements Stadium | | |
| 2022-10-15 15:00:0015/10/22 | Esh Winning v Washington | 15:00:003:00 pm | Division 2 | 2022-23 | The WindowsPlusRoofs Arena | | |
| 2022-10-22 15:00:0022/10/22 | Chester-le-Street United v Esh Winning | 15:00:003:00 pm | Division 2 | 2022-23 | Ford Hub Sports Complex | | |
| 2022-10-25 19:30:0025/10/22 | Chester-le-Street Town v Esh Winning | 19:30:007:30 pm | Division 2 | 2022-23 | Moor Park | | |
| 2022-10-29 15:00:0029/10/22 | Esh Winning v Horden CW | 15:00:003:00 pm | Division 2 | 2022-23 | The WindowsPlusRoofs Arena | | |
| 2022-11-05 15:00:0005/11/22 | Willington v Esh Winning | 15:00:003:00 pm | Division 2 | 2022-23 | Hall Lane | | |
| 2022-11-12 15:00:0012/11/22 | Esh Winning v Boldon CA | 15:00:003:00 pm | Division 2 | 2022-23 | The WindowsPlusRoofs Arena | | |
| 2022-11-19 15:00:0019/11/22 | Bedlington Terriers v Esh Winning | 15:00:003:00 pm | Division 2 | 2022-23 | Doctor Pit Park | | |
| 2022-11-26 15:00:0026/11/22 | Esh Winning v Sunderland West End | 15:00:003:00 pm | Division 2 | 2022-23 | The WindowsPlusRoofs Arena | | |
| 2022-12-03 15:00:0003/12/22 | Esh Winning v Boro Rangers | 15:00:003:00 pm | Division 2 | 2022-23 | The WindowsPlusRoofs Arena | | |
| 2022-12-10 15:00:0010/12/22 | Billingham Town v Esh Winning | 15:00:003:00 pm | Division 2 | 2022-23 | Bedford Terrace | | |
| 2022-12-17 15:00:0017/12/22 | Esh Winning v Chester-le-Street Town | 15:00:003:00 pm | Division 2 | 2022-23 | The WindowsPlusRoofs Arena | | |
| 2023-01-07 15:00:0007/01/23 | Washington v Esh Winning | 15:00:003:00 pm | Division 2 | 2022-23 | Northern Area Playing Fields | | |
| 2023-01-14 15:00:0014/01/23 | Esh Winning v Brandon United | 15:00:003:00 pm | Division 2 | 2022-23 | The WindowsPlusRoofs Arena | | |
| 2023-01-21 15:00:0021/01/23 | Easington Colliery v Esh Winning | 15:00:003:00 pm | Division 2 | 2022-23 | Easington Welfare Park | | |
| 2023-01-28 15:00:0028/01/23 | Esh Winning v Billingham Synthonia | 15:00:003:00 pm | Division 2 | 2022-23 | The WindowsPlusRoofs Arena | | |
| 2023-02-04 15:00:0004/02/23 | Redcar Town v Esh Winning | 15:00:003:00 pm | Division 2 | 2022-23 | The Vibrant Stadium | | |
| 2023-02-11 15:00:0011/02/23 | Esh Winning v Prudhoe YC Seniors | 15:00:003:00 pm | Division 2 | 2022-23 | The WindowsPlusRoofs Arena | | |
| 2023-02-18 15:00:0018/02/23 | Blyth Town v Esh Winning | 15:00:003:00 pm | Division 2 | 2022-23 | Gateway Park | | |
| 2023-02-25 15:00:0025/02/23 | Newcastle University v Esh Winning | 15:00:003:00 pm | Division 2 | 2022-23 | Essity Park | | |
| 2023-03-04 15:00:0004/03/23 | Esh Winning v Easington Colliery | 15:00:003:00 pm | Division 2 | 2022-23 | The WindowsPlusRoofs Arena | | |
| 2023-03-25 15:00:0025/03/23 | Ryton & Crawcrook Albion v Esh Winning | 15:00:003:00 pm | Division 2 | 2022-23 | Kingsley Park | | |
| 2023-04-01 15:00:0001/04/23 | Brandon United v Esh Winning | 15:00:003:00 pm | Division 2 | 2022-23 | Welfare Ground | | |
| 2023-04-08 15:00:0008/04/23 | Esh Winning v Birtley Town | 15:00:003:00 pm | Division 2 | 2022-23 | The WindowsPlusRoofs Arena | | |
| 2023-04-11 15:00:0011/04/23 | Boro Rangers v Esh Winning | 15:00:003:00 pm | Division 2 | 2022-23 | Stokesley Sports Club | | |
| 2023-04-15 15:00:0015/04/23 | Jarrow v Esh Winning | 15:00:003:00 pm | Division 2 | 2022-23 | Perth Green CA | | |
| 2023-04-22 15:00:0022/04/23 | Esh Winning v Chester-le-Street United | 15:00:003:00 pm | Division 2 | 2022-23 | The WindowsPlusRoofs Arena | | |
