| 2021-06-26 10:00:00Sat 26/06 | Mallaig | 4 - 3 | Portree | Mallaig |
| 2021-06-26 15:00:00Sat 26/06 | Portree Juniors | 3 - 0 | Kyle | Portree |
| 2021-06-26 15:00:00Sat 26/06 | Kyleakin | 7 - 1 | Glenelg | Kyleakin |
| 2021-06-26 18:00:00Sat 26/06 | Sleat & Strath | 2 - 4 | NW Skye | Broadford |
| 2021-07-03 15:00:00Sat 03/07 | Kyle | 1 - 4 | Portree | Kyle |
| 2021-07-03 15:00:00Sat 03/07 | NW Skye | 1 - 1 | Mallaig | Uig |
| 2021-07-03 15:00:00Sat 03/07 | Portree Juniors | 1 - 3 | Kyleakin | Portree |
| 2021-07-03 18:00:00Sat 03/07 | Glenelg | 1 - 5 | Sleat & Strath | Glenelg |
| 2021-07-10 12:00:00Sat 10/07 | Mallaig | 3 - 1 | Glenelg | Mallaig |
| 2021-07-10 15:00:00Sat 10/07 | Kyleakin | 5 - 1 | Kyle | Kyleakin |
| 2021-07-10 15:00:00Sat 10/07 | Sleat & Strath | 8 - 1 | Portree Juniors | Broadford |
| 2021-07-10 18:00:00Sat 10/07 | Portree | 1 - 1 | NW Skye | Portree |
| 2021-07-17 15:00:00Sat 17/07 | Portree Juniors | 1 - 5 | Mallaig | Portree |
| 2021-07-17 15:00:00Sat 17/07 | Kyleakin | 1 - 1 | Sleat & Strath | Kyleakin |
| 2021-07-17 15:00:00Sat 17/07 | Kyle | 2 - 1 | NW Skye | Kyle |
| 2021-07-17 18:00:00Sat 17/07 | Glenelg | 3 - 2 | Portree | Glenelg |
| 2021-07-24 14:00:00Sat 24/07 | Mallaig | 2 - 0 | Kyleakin | Mallaig |
| 2021-07-31 14:00:00Sat 31/07 | Sleat & Strath | 3 - 1 | Mallaig | Broadford |
| 2021-07-31 15:00:00Sat 31/07 | Kyle | 4 - 3 | Glenelg | Kyle |
| 2021-07-31 15:00:00Sat 31/07 | Kyleakin | 3 - 0 | Portree | Kyleakin |
| 2021-07-31 16:00:00Sat 31/07 | Portree Juniors | 1 - 2 | NW Skye | Portree |
| 2021-08-07 14:00:00Sat 07/08 | Mallaig | 4 - 0 | Kyle | Mallaig |
| 2021-08-07 15:00:00Sat 07/08 | Glenelg | 1 - 3 | Portree Juniors | Glenelg |
| 2021-08-07 15:00:00Sat 07/08 | NW Skye | 3 - 3 | Kyleakin | Uig |
| 2021-08-07 18:00:00Sat 07/08 | Portree | 0 - 10 | Sleat & Strath | Portree |
| 2021-08-14 15:00:00Sat 14/08 | Portree | 4 - 2 | Portree Juniors | Portree |
| 2021-08-14 18:00:00Sat 14/08 | Sleat & Strath | 5 - 1 | Kyle | Broadford |
| 2021-08-14 18:30:00Sat 14/08 | NW Skye | 5 - 0 | Glenelg | Uig |
| 2021-08-21 15:00:00Sat 21/08 | Glenelg | 2 - 0 | Kyleakin | Glenelg |
| 2021-08-21 15:00:00Sat 21/08 | Kyle | 3 - 2 | Portree Juniors | Kyle |
| 2021-08-21 15:00:00Sat 21/08 | Portree | 1 - 2 | Mallaig | Portree KG5 |
| 2021-08-21 18:00:00Sat 21/08 | NW Skye | 3 - 5 | Sleat & Strath | Uig |
| 2021-08-28 15:00:00Sat 28/08 | Portree | 0 - 0 | Kyle | Portree KG5 |
| 2021-08-28 15:00:00Sat 28/08 | Mallaig | 3 - 3 | NW Skye | Mallaig |
| 2021-08-28 15:00:00Sat 28/08 | Kyleakin | 9 - 1 | Portree Juniors | Kyleakin |
| 2021-08-31 18:30:00Tue 31/08 | Sleat & Strath | 5 - 1 | Glenelg | Broadford |
| 2021-09-03 18:30:00Fri 03/09 | NW Skye | 5 - 0 | Portree | Uig |
| 2021-09-04 14:30:00Sat 04/09 | Glenelg | 4 - 5 | Mallaig | Glenelg |
| 2021-09-04 15:00:00Sat 04/09 | Kyle | 2 - 6 | Kyleakin | Kyle |
| 2021-09-11 14:15:00Sat 11/09 | Mallaig | 7 - 1 | Portree Juniors | Mallaig |
| 2021-09-11 15:00:00Sat 11/09 | NW Skye | 4 - 0 | Kyle | Portree |
| 2021-09-11 15:00:00Sat 11/09 | Sleat & Strath | 5 - 0 | Kyleakin | Broadford |
| 2021-09-11 17:00:00Sat 11/09 | Portree | 3 - 1 | Glenelg | Portree KG5 |
| 2021-09-14 18:15:00Tue 14/09 | Portree Juniors | 1 - 7 | Sleat & Strath | Portree KG5 |
| 2021-09-18 14:00:00Sat 18/09 | Kyleakin | 0 - 1 | Mallaig | Kyleakin |
| 2021-09-18 15:00:00Sat 18/09 | Portree Juniors | 5 - 3 | Portree | Portree KG5 |
| 2021-09-18 15:00:00Sat 18/09 | Kyle | 0 - 10 | Sleat & Strath | Kyle |
| 2021-09-25 12:00:00Sat 25/09 | Portree | 1 - 6 | Kyleakin | Portree High School |
| 2021-09-25 14:00:00Sat 25/09 | Mallaig | 2 - 2 | Sleat & Strath | Mallaig |
| 2021-09-25 15:00:00Sat 25/09 | NW Skye | 1 - 3 | Portree Juniors | Uig |
| 2021-10-02 14:00:00Sat 02/10 | Portree Juniors | 3 - 1 | Glenelg | Portree High School |
| 2021-10-02 14:00:00Sat 02/10 | Kyle | 1 - 6 | Mallaig | Plockton |
| 2021-10-02 16:00:00Sat 02/10 | Kyleakin | 0 - 6 | NW Skye | Kyleakin |
| 2021-10-02 17:00:00Sat 02/10 | Sleat & Strath | 8 - 0 | Portree | Plockton |
| 2021-10-09 15:00:00Sat 09/10 | Glenelg | 8 - 1 | Kyle | Glenelg |
| 2021-10-16 16:00:00Sat 16/10 | Glenelg | 1 - 4 | NW Skye | Glenelg |
