| Date | Home | Time/Results | Away | League | Season | Venue | Article | Match Day | Attendance | Captain |
|---|---|---|---|---|---|---|---|---|---|---|
| Saltburn Athletic | 1 - 5 | Guisborough Town U14 Whites | TJFA U14 Division 3 | 2020/21 | Recap | - | - | - | ||
| Guisborough Town U14 Whites | 2 - 1 | Riverside Juniors U14 FC | TJFA U14 Division 3 | 2020/21 | Recap | - | - | - | ||
| Eaglescliffe Elementis Juniors U14 Blue | 2 - 1 | Guisborough Town U14 Whites | TJFA U14 Division 3 | 2020/21 | Recap | - | - | - | ||
| Seaton Carew Lions | 1 - 2 | Guisborough Town U14 Whites | TJFA U14 Division 3 | 2020/21 | Recap | - | - | - | ||
| Guisborough Town U14 Whites | Redcar Town Royals | TJFA U14 Division 3 | 2020/21 | Recap | - | - | - | |||
| Whinney Banks YCC Juniors U14 | Guisborough Town U14 Whites | TJFA U14 Division 3 | 2020/21 | Recap | - | - | - | |||
| Guisborough Town U14 Whites | Redcar Town Royals | TJFA U14 Division 3 | 2020/21 | Recap | - | - | - | |||
| Guisborough Town U14 Whites | 2 - 0 | Whinney Banks YCC Juniors U14 | TJFA U14 Division 3 | 2020/21 | Recap | - | - | - | ||
| Riverside Juniors U14 FC | 1 - 2 | Guisborough Town U14 Whites | TJFA U14 Division 3 | 2020/21 | Recap | - | - | - | ||
| South Park Rangers Reds | 2 - 1 | Guisborough Town U14 Whites | TJFA U14 Division 3 | 2020/21 | Recap | - | - | - | ||
| Guisborough Town U14 Whites | 2 - 4 | Seaton Carew Lions | TJFA U14 Division 3 | 2020/21 | Recap | - | - | - | ||
| Guisborough Town U14 Whites | 1 - 1 | TJFA U14 Division 3 | 2020/21 | Recap | - | - | - | |||
| Stockton Town Youth U14 Blues | 3 - 1 | Guisborough Town U14 Whites | TJFA U14 Division 3 | 2020/21 | Recap | - | - | - | ||
| Guisborough Town U14 Whites | 1 - 3 | Eaglescliffe Elementis Juniors U14 Blue | TJFA U14 Division 3 | 2020/21 | Recap | - | - | - | ||
| Guisborough Town U14 Whites | 4 - 1 | South Park Rangers Reds | TJFA U14 Division 3 | 2020/21 | Recap | - | - | - | ||
| Guisborough Town U14 Whites | 3 - 0 | Saltburn Athletic | TJFA U14 Division 3 | 2020/21 | Recap | - | - | - | ||
| Guisborough Town U14 Whites | P - P | Stockton Town Youth U14 Blues | TJFA U14 Division 3 | 2020/21 | Recap | - | - | - |
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