Coming soon…
| Date | Home | Time/Results | Away | League | Venue | Article | Attendance | Captain |
|---|---|---|---|---|---|---|---|---|
| Bishop Auckland St. Marys Aces | Guisborough Town U16 | TJFA U16 Division 2 | Preview | - | - | |||
| Saltburn Athletic Dolphins | Guisborough Town U16 | TJFA U16 Division 2 | Preview | - | - | |||
| Ferryhill Town Wanderers | Guisborough Town U16 | TJFA U16 Division 2 | Preview | - | - | |||
| Guisborough Town U16 | Grangetown Boys Club | TJFA U16 Division 2 | Preview | - | - | |||
| Guisborough Town U16 | Whitby Fishermen | TJFA U16 Division 2 | Preview | - | - | |||
| Guisborough Town U16 | Bishop Auckland St. Marys Aces | TJFA U16 Division 2 | Preview | - | - | |||
| North Ormesby | Guisborough Town U16 | TJFA U16 Division 2 | Preview | - | - | |||
| Guisborough Town U16 | Ferryhill Town Wanderers | TJFA U16 Division 2 | Preview | - | - | |||
| Thirsk Falcons | Guisborough Town U16 | TJFA U16 Division 2 | Preview | - | - | |||
| Guisborough Town U16 | Darlington Young Bulls | TJFA U16 Division 2 | Preview | - | - | |||
| Grangetown Boys Club | Guisborough Town U16 | TJFA U16 Division 2 | Recap | - | - | |||
| Guisborough Town U16 | Saltburn Athletic Dolphins | TJFA U16 Division 2 | Recap | - | - | |||
| Darlington Young Bulls | Guisborough Town U16 | TJFA U16 Division 2 | Recap | - | - | |||
| Guisborough Town U16 | Copmanthorpe U16 | North Riding U16 County Cup | Recap | - | - | |||
| Guisborough Town U16 | 2 - 5 | North Ormesby | TJFA U16 Division 2 | Recap | - | - | ||
| Guisborough Town U16 | 5 - 0 | Hartlepool Pools Youth | TJFA U16 Division 2 | Recap | - | - | ||
| Whitby Fishermen | 1 - 0 | Guisborough Town U16 | TJFA U16 Division 2 | Recap | - | - | ||
| Guisborough Town U16 | 8 - 1 | Cargo Fleet Juniors | North Riding U16 County Cup | Recap | - | - | ||
| Guisborough Town U16 | 4 - 1 | Thirsk Falcons | TJFA U16 Division 2 | Recap | - | - | ||
| Hartlepool Pools Youth | 2 - 5 | Guisborough Town U16 | TJFA U16 Division 2 | Recap | - | - |
