| 2020-09-05 15:00:0005/09/20 | Esh Winning v Brandon United | 3 - 2 | Division 2 | 2020-21 | The WindowsPlusRoofs Arena | | 119 |
| Jay McLean (41,76) Channon North (54) |
| Kai Hewitson (3) Connor Brown (75) |
| 2020-09-09 19:45:0009/09/20 | Redcar Athletic v Esh Winning | 1 - 0 | Division 2 | 2020-21 | Green Lane | | 298 |
| Lee Bythway (62) |
| 2020-09-12 15:00:0012/09/20 | Carlisle City v Esh Winning | 2 - 1 | Division 2 | 2020-21 | Gillford Park Stadium | | 89 |
| Robert McCartney (44) Ben Palmer (62) |
| Matthew Allison (67) |
| 2020-09-17 19:30:0017/09/20 | Esh Winning v Ryton & Crawcrook Albion | 1 - 0 | Division 2 | 2020-21 | The WindowsPlusRoofs Arena | | 141 |
| Channon North (88) |
| Michael Stephenson sent off (66) |
| 2020-09-23 19:30:0023/09/20 | Billingham Synthonia v Esh Winning | 5 - 0 | Division 2 | 2020-21 | Norton (Teesside) Sports Complex | | 80 |
| James Rowe (3) Joe Scaife-Wheatley (15) Kurtis Howes 2 (39, 59) Benjamin Jackson (45+2) |
| 2020-09-26 15:00:0026/09/20 | Esh Winning v Heaton Stannington | 2 - 4 | Division 2 | 2020-21 | The WindowsPlusRoofs Arena | | 91 |
| Max Stoker (10) Channon North (27) |
| Jonathan Wright (62 pen) Lewis Burns (71) Kevin Carr (77) Richard Hoggins (96) |
| 2020-10-01 19:30:0001/10/20 | Esh Winning v Washington | 2 - 1 | Division 2 | 2020-21 | The WindowsPlusRoofs Arena | | 103 |
| Channon North 2 (25 pen, 47) |
| Jack Warriner (59) |
| 2020-10-03 15:00:0003/10/20 | Willington v Esh Winning | 1 - 6 | Division 2 | 2020-21 | Hall Lane | | 115 |
| Lewis Martin (10) |
| Max Stoker 2 (2, 50) Callum Boakes 2 (25, 80) Channon North 2 (35, 42) |
| 2020-10-10 15:00:4510/10/20 | Esh Winning v AFC Blackpool | 1 - 2 | | 2020-21 | The WindowsPlusRoofs Arena | FA VaseSecond Qualifying Round | 91 |
| Lee McMahon (9), Matthew Allison sent off (76) |
| Benjamin Duffield 2 (30, 70) Bily McKenna sent off (68 |
| 2020-10-17 15:00:0017/10/20 | Esh Winning v Birtley Town | 1 - 3 | Division 2 | 2020-21 | The WindowsPlusRoofs Arena | | 71 |
| Jay McClean (65) |
| Jack Honour 2 (20, 33 pen) Joe Barwick (76) |
| 2020-10-22 19:30:0022/10/20 | Esh Winning v Chester-le-Street | 2 - 4 | Division 2 | 2020-21 | The WindowsPlusRoofs Arena | | 121 |
| Max Stoker (15) Jay McLean (56), Jamie McLeod sent off (69) Thomas Orton sent off (90) |
| Liam Dixon (49) Craig Marron (51 pen) Joshua Akel (70) Owen Henderson (80) |
| 2020-10-24 15:00:0024/10/20 | Easington Colliery v Esh Winning | 15:00:003:00 pm | Division 2 | 2020-21 | Welfare Park | | |
| 2020-10-31 15:00:0031/10/20 | Esh Winning v Bedlington Terriers | 15:00:003:00 pm | Division 2 | 2020-21 | The WindowsPlusRoofs Arena | | |
| 2020-11-07 15:00:0007/11/20 | Esh Winning v Crook Town | 15:00:003:00 pm | Division 2 | 2020-21 | The WindowsPlusRoofs Arena | | |
| 2020-11-14 15:00:0014/11/20 | Esh Winning v Newcastle University | 15:00:003:00 pm | Division 2 | 2020-21 | The WindowsPlusRoofs Arena | | |
| 2020-11-21 15:00:0021/11/20 | West Allotment Celtic v Esh Winning | 15:00:003:00 pm | Division 2 | 2020-21 | Sam Smith's Park | | |
| 2020-11-28 15:00:0028/11/20 | Esh Winning v Durham City | 15:00:003:00 pm | Division 2 | 2020-21 | The WindowsPlusRoofs Arena | | |
| 2020-12-02 19:45:0002/12/20 | Sunderland West End v Esh Winning | 19:45:007:45 pm | Division 2 | 2020-21 | Ford Hub Sports Complex | | |
| 2020-12-05 15:00:0005/12/20 | Esh Winning v Jarrow | 15:00:003:00 pm | Division 2 | 2020-21 | The WindowsPlusRoofs Arena | | |
| 2020-12-12 15:00:0012/12/20 | Tow Law Town v Esh Winning | 15:00:003:00 pm | Division 2 | 2020-21 | Ironworks Road | | |
| 2020-12-19 15:00:0019/12/20 | Esh Winning v Redcar Athletic | 15:00:003:00 pm | Division 2 | 2020-21 | The WindowsPlusRoofs Arena | | |
| 2020-12-26 15:00:0026/12/20 | Birtley Town v Esh Winning | 15:00:003:00 pm | Division 2 | 2020-21 | The Arrowmark Home Improvements Stadium | | |
| 2021-01-02 15:00:0002/01/21 | Esh Winning v Easington Colliery | 15:00:003:00 pm | Division 2 | 2020-21 | The WindowsPlusRoofs Arena | | |
| 2021-01-09 15:00:0009/01/21 | Ryton & Crawcrook Albion v Esh Winning | 15:00:003:00 pm | Division 2 | 2020-21 | Kingsley Park | | |
| 2021-01-16 15:00:0016/01/21 | Esh Winning v Billingham Synthonia | 15:00:003:00 pm | Division 2 | 2020-21 | The WindowsPlusRoofs Arena | | |
| 2021-01-23 15:00:0023/01/21 | Washington v Esh Winning | 15:00:003:00 pm | Division 2 | 2020-21 | Ford Hub Sports Complex | | |
| 2021-01-30 15:00:0030/01/21 | Chester-le-Street v Esh Winning | 15:00:003:00 pm | Division 2 | 2020-21 | Moor Park | | |
| 2021-02-06 15:00:0006/02/21 | Brandon United v Esh Winning | 15:00:003:00 pm | Division 2 | 2020-21 | Welfare Ground | | |
| 2021-02-13 15:00:0013/02/21 | Esh Winning v Carlisle City | 15:00:003:00 pm | Division 2 | 2020-21 | The WindowsPlusRoofs Arena | | |
| 2021-02-20 15:00:0020/02/21 | Heaton Stannington v Esh Winning | 15:00:003:00 pm | Division 2 | 2020-21 | Grounsell Park | | |
| 2021-02-27 15:00:0027/02/21 | Esh Winning v Willington | 15:00:003:00 pm | Division 2 | 2020-21 | The WindowsPlusRoofs Arena | | |
| 2021-03-06 15:00:0006/03/21 | Esh Winning v Sunderland West End | 15:00:003:00 pm | Division 2 | 2020-21 | The WindowsPlusRoofs Arena | | |
| 2021-03-13 15:00:0013/03/21 | Bedlington Terriers v Esh Winning | 15:00:003:00 pm | Division 2 | 2020-21 | Doctor Pit Park | | |
| 2021-03-20 15:00:0020/03/21 | Crook Town v Esh Winning | 15:00:003:00 pm | Division 2 | 2020-21 | The Sir Tom Cowie Millfield | | |
| 2021-03-27 15:00:0027/03/21 | Newcastle University v Esh Winning | 15:00:003:00 pm | Division 2 | 2020-21 | Kimberley Park | | |
| 2021-04-03 15:00:0003/04/21 | Esh Winning v West Allotment Celtic | 15:00:003:00 pm | Division 2 | 2020-21 | The WindowsPlusRoofs Arena | | |
| 2021-04-10 15:00:0010/04/21 | Durham City v Esh Winning | 15:00:003:00 pm | Division 2 | 2020-21 | Hall Lane | | |
| 2021-04-17 15:00:0017/04/21 | Jarrow v Esh Winning | 15:00:003:00 pm | Division 2 | 2020-21 | Perth Green CA | | |
| 2021-04-24 15:00:0024/04/21 | Esh Winning v Tow Law Town | 15:00:003:00 pm | Division 2 | 2020-21 | The WindowsPlusRoofs Arena | | |
