| 2019-08-03 15:00:0003/08/19 | Seaham Red Star v Guisborough Town | 0 - 2 | Division 1 | 2019-20 | The Ferguson Motor Repairs Stadium | | 115 |
| John Howard (41), Joe Ferguson (88) |
| 2019-08-07 19:45:0007/08/19 | Guisborough Town v Sunderland RCA | 1 - 2 | Division 1 | 2019-20 | King George V Ground | | 301 |
| Daniel Earl (8) |
| Kyle Davis (17) Greg Swansbury (23) |
| 2019-08-10 15:00:0010/08/19 | North Shields v Guisborough Town | 2 - 2 | | 2019-20 | Daren Persson Stadium | FA CupExtra Preliminary Round Qualifying | 250 |
| Connor Campbell 2 (10, 44) |
| Charlie Marshall (81), Daniel Earl (87) |
| 2019-08-14 19:45:0014/08/19 | Guisborough Town v North Shields | 1 - 0 | | 2019-20 | King George V Ground | FA CupExtra Preliminary Round Qualifying - Replay | 304 |
| Steven Roberts (78), , Sonni Coleman missed penalty (19) |
| 2019-08-17 15:00:0017/08/19 | Hebburn Town v Guisborough Town | 1 - 2 | Division 1 | 2019-20 | The Energy Check Sports Ground | | 312 |
| Michael Richardson (45) |
| Sonni Coleman 2 (3, 19) |
| 2019-08-21 19:45:0021/08/19 | Guisborough Town v West Auckland Town | 1 - 0 | Division 1 | 2019-20 | King George V Ground | | 303 |
| Matthew Crust (33) |
| 2019-08-24 15:00:0024/08/19 | Seaham Red Star v Guisborough Town | 3 - 1 | | 2019-20 | The Ferguson Motor Repairs Stadium | FA CupPreliminary Round Qualifying | 128 |
| Richard Coulson (69) Daniel Wilson (77) Morgan Dart (90), Liam Gillesphey sent off |
| Mason McNeil (49) |
| 2019-08-26 11:00:0026/08/19 | Northallerton Town v Guisborough Town | 0 - 3 | Division 1 | 2019-20 | The Calvert Stadium | | 244 |
| James Rowe missed pen (78) |
| Danny Earl (34) Lewis Hawkins (52) Mark Robinson (58 pen) |
| 2019-08-31 15:00:0031/08/19 | Penrith v Guisborough Town | 0 - 1 | | 2019-20 | The Frenchfield Stadium | FA VaseFirst Qualifying Round | 135 |
| Sonni Coleman (47) |
| 2019-09-04 19:45:0004/09/19 | Guisborough Town v Whitley Bay | 1 - 0 | Division 1 | 2019-20 | King George V Ground | | 301 |
| OG (27) |
| 2019-09-07 15:00:0007/09/19 | Billingham Town v Guisborough Town | 1 - 0 | Division 1 | 2019-20 | Bedford Terrace | | 262 |
| Craig Hutchinson (93) |
| 2019-09-10 19:30:0010/09/19 | Shildon v Guisborough Town | 2 - 1 | League Cup - Group F | 2019-20 | Dean Street | | 168 |
| Tafari Nicholas 2 (50, 54) |
| Steven Roberts (86) |
| 2019-09-14 15:00:0014/09/19 | Albion Sports v Guisborough Town | 1 - 5 | | 2019-20 | Throstle Nest | FA VaseSecond Qualifying Round | 56 |
| Alhassane Keita (60) |
| Mason McNeil 2 (21, 29) Mark Robinson (35 pen) Sonni Coleman (66) Thomas Marror (85) |
| 2019-09-17 19:30:0017/09/19 | Consett v Guisborough Town | 5 - 2 | Division 1 | 2019-20 | Belle View Stadium | | 368 |
| Ross Wilkinson (3) Calvin Smith (8) Dale Pearson 2 (38, 62) Matthew Lovatt (76 og) |
| Charlie Marshall (14) Mark Robinson (67 pen) |
| 2019-09-21 15:00:0021/09/19 | Guisborough Town v Ashington | 15:00:003:00 pm | Division 1 | 2019-20 | King George V Ground | | |
| 2019-09-25 19:45:0025/09/19 | Guisborough Town v Carlisle City | 19:45:007:45 pm | League Cup - Group F | 2019-20 | King George V Ground | | |
| 2019-09-28 15:00:0028/09/19 | Newcastle Benfield v Guisborough Town | 15:00:003:00 pm | Division 1 | 2019-20 | Sam Smith's Park | | |
| 2019-10-05 15:00:0005/10/19 | Guisborough Town v Stockton Town | 15:00:003:00 pm | Division 1 | 2019-20 | King George V Ground | | |
| 2019-10-08 19:30:0008/10/19 | Tow Law Town v Guisborough Town | 19:30:007:30 pm | League Cup - Group F | 2019-20 | Ironworks Road | | |
| 2019-10-16 19:45:0016/10/19 | Guisborough Town v Willington | 19:45:007:45 pm | League Cup - Group F | 2019-20 | King George V Ground | | |
| 2019-10-26 15:00:0026/10/19 | Guisborough Town v North Shields | 15:00:003:00 pm | Division 1 | 2019-20 | King George V Ground | | |
| 2019-11-02 15:00:0002/11/19 | Thornaby v Guisborough Town | 15:00:003:00 pm | Division 1 | 2019-20 | Teesdale Park | | |
| 2019-11-06 19:45:0006/11/19 | Guisborough Town v Bishop Auckland | 19:45:007:45 pm | Division 1 | 2019-20 | King George V Ground | | |
| 2019-11-09 15:00:0009/11/19 | Guisborough Town v Whickham | 15:00:003:00 pm | Division 1 | 2019-20 | King George V Ground | | |
| 2019-11-16 15:00:0016/11/19 | Newton Aycliffe v Guisborough Town | 15:00:003:00 pm | Division 1 | 2019-20 | The Beaumont Landscapes Stadium | | |
| 2019-11-23 15:00:0023/11/19 | Guisborough Town v Shildon | 15:00:003:00 pm | Division 1 | 2019-20 | King George V Ground | | |
| 2019-11-27 19:45:0027/11/19 | Guisborough Town v Sunderland Ryhope C.W. | 19:45:007:45 pm | Division 1 | 2019-20 | King George V Ground | | |
| 2019-11-30 15:00:0030/11/19 | Sunderland RCA v Guisborough Town | 15:00:003:00 pm | Division 1 | 2019-20 | Sunderland LGV Park | | |
| 2019-12-07 15:00:0007/12/19 | Guisborough Town v Consett | 15:00:003:00 pm | Division 1 | 2019-20 | King George V Ground | | |
| 2019-12-14 15:00:0014/12/19 | West Auckland Town v Guisborough Town | 15:00:003:00 pm | Division 1 | 2019-20 | Wanted Stadium | | |
| 2019-12-26 11:00:0026/12/19 | Guisborough Town v Northallerton Town | 11:00:0011:00 am | Division 1 | 2019-20 | King George V Ground | | |
| 2020-01-04 15:00:0004/01/20 | Guisborough Town v Seaham Red Star | 15:00:003:00 pm | Division 1 | 2019-20 | King George V Ground | | |
| 2020-01-11 15:00:0011/01/20 | Whitley Bay v Guisborough Town | 15:00:003:00 pm | Division 1 | 2019-20 | Hillheads Park | | |
| 2020-01-18 15:00:0018/01/20 | Guisborough Town v Hebburn Town | 15:00:003:00 pm | Division 1 | 2019-20 | King George V Ground | | |
| 2020-01-25 15:00:0025/01/20 | Penrith v Guisborough Town | 15:00:003:00 pm | Division 1 | 2019-20 | The Frenchfield Stadium | | |
| 2020-02-01 15:00:0001/02/20 | Guisborough Town v Billingham Town | 15:00:003:00 pm | Division 1 | 2019-20 | King George V Ground | | |
| 2020-02-08 15:00:0008/02/20 | Bishop Auckland v Guisborough Town | 15:00:003:00 pm | Division 1 | 2019-20 | Heritage Park | | |
| 2020-02-15 15:00:0015/02/20 | Ashington v Guisborough Town | 15:00:003:00 pm | Division 1 | 2019-20 | Woodhorn Lane | | |
| 2020-02-22 15:00:0022/02/20 | Guisborough Town v Newcastle Benfield | 15:00:003:00 pm | Division 1 | 2019-20 | King George V Ground | | |
| 2020-02-29 15:00:0029/02/20 | Stockton Town v Guisborough Town | 15:00:003:00 pm | Division 1 | 2019-20 | The Coverall Stadium | | |
| 2020-03-07 15:00:0007/03/20 | Sunderland Ryhope C.W. v Guisborough Town | 15:00:003:00 pm | Division 1 | 2019-20 | Ryhope Recreation Ground | | |
| 2020-03-14 15:00:0014/03/20 | Guisborough Town v Penrith | 15:00:003:00 pm | Division 1 | 2019-20 | King George V Ground | | |
| 2020-03-21 15:00:0021/03/20 | North Shields v Guisborough Town | 15:00:003:00 pm | Division 1 | 2019-20 | Daren Persson Stadium | | |
| 2020-03-28 15:00:0028/03/20 | Guisborough Town v Thornaby | 15:00:003:00 pm | Division 1 | 2019-20 | King George V Ground | | |
| 2020-04-04 15:00:0004/04/20 | Whickham v Guisborough Town | 15:00:003:00 pm | Division 1 | 2019-20 | Glebe Sports Ground | | |
| 2020-04-11 15:00:0011/04/20 | Guisborough Town v Newton Aycliffe | 15:00:003:00 pm | Division 1 | 2019-20 | King George V Ground | | |
| 2020-04-18 15:00:0018/04/20 | Shildon v Guisborough Town | 15:00:003:00 pm | Division 1 | 2019-20 | Dean Street | | |
