| 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 | 7 - 0 | Division 2 | 2020-21 | Welfare Park | | 106 |
| Jack Pounder 4 (14, 16, 20, 31) Josh Home-Jackson (21) Connor Slack (53) Callum Banki (55 og) |
| 2020-10-31 15:00:0031/10/20 | Esh Winning v Bedlington Terriers | 4 - 1 | Division 2 | 2020-21 | The WindowsPlusRoofs Arena | | 52 |
| Lee McMahon (11) Matthew Soulsby (19) Callum Banki (31) Callum Boakes (68) |
| Liam Anderson (52), Matty Fisher missed pen (52) |
| 2020-12-06 19:30:5806/12/20 | Esh Winning v Bishop Auckland | 19:30:587:30 pm | | 2020-21 | The WindowsPlusRoofs Arena | Durham Challenge CupFirst Round | |
