| 2019-04-06 13:30:00Sat 06/04 | Mallaig | 3 - 0 | Portree | Mallaig |
| 2019-04-06 15:00:00Sat 06/04 | GA United | 3 - 4 | Kyleakin | Gairloch |
| 2019-04-06 18:00:00Sat 06/04 | Portree Juniors | 8 - 0 | Glenelg | Portree High School |
| 2019-04-06 18:00:00Sat 06/04 | Sleat & Strath | 3 - 1 | NW Skye | Broadford |
| 2019-04-13 14:30:00Sat 13/04 | Mallaig | 9 - 0 | GA United | Mallaig |
| 2019-04-13 18:00:00Sat 13/04 | Kyleakin | 3 - 1 | NW Skye | Kyleakin |
| 2019-04-19 18:45:00Fri 19/04 | Kyle | 1 - 8 | Sleat & Strath | Kyle |
| 2019-04-20 17:00:00Sat 20/04 | GA United | 1 - 2 | Portree | Gairloch |
| 2019-04-20 18:00:00Sat 20/04 | Kyleakin | 1 - 1 | Portree Juniors | Kyleakin |
| 2019-04-20 18:00:00Sat 20/04 | NW Skye | 3 - 5 | Mallaig | Uig |
| 2019-04-27 18:00:00Sat 27/04 | Portree | 7 - 1 | Glenelg | Portree High School |
| 2019-04-27 18:00:00Sat 27/04 | Kyleakin | 6 - 2 | Kyle | Kyleakin |
| 2019-05-01 19:00:00Wed 01/05 | Glenelg | 4 - 2 | Kyle | Glenelg |
| 2019-05-01 19:15:00Wed 01/05 | Sleat & Strath | 3 - 2 | Portree Juniors | Broadford |
| 2019-05-03 19:00:00Fri 03/05 | NW Skye | 3 - 3 | Portree | Uig |
| 2019-05-04 18:00:00Sat 04/05 | Glenelg | 0 - 12 | Sleat & Strath | Glenelg |
| 2019-05-18 14:00:00Sat 18/05 | Portree Juniors | 1 - 3 | GA United | Portree High School |
| 2019-05-21 19:00:00Tue 21/05 | Kyle | 1 - 4 | Mallaig | Kyle |
| 2019-05-24 19:15:00Fri 24/05 | Portree | 8 - 2 | Kyle | King George V, Portree |
| 2019-05-28 19:00:00Tue 28/05 | Glenelg | 1 - 3 | Kyleakin | Glenelg |
| 2019-05-28 19:15:00Tue 28/05 | NW Skye | 2 - 1 | Portree Juniors | Uig |
| 2019-05-28 19:30:00Tue 28/05 | Portree | 1 - 6 | Sleat & Strath | Portree High School |
| 2019-05-29 19:30:00Wed 29/05 | Kyle | 1 - 6 | GA United | Kyle |
| 2019-05-31 19:00:00Fri 31/05 | Glenelg | 0 - 4 | Mallaig | Glenelg |
| 2019-06-01 18:00:00Sat 01/06 | Kyle | 1 - 11 | NW Skye | Kyle |
| 2019-06-01 18:00:00Sat 01/06 | Sleat & Strath | 6 - 2 | Kyleakin | Broadford |
| 2019-06-05 19:30:00Wed 05/06 | Portree | 3 - 2 | Portree Juniors | Portree High School |
| 2019-06-08 18:00:00Sat 08/06 | NW Skye | 5 - 0 | Glenelg | Uig |
| 2019-06-14 19:30:00Fri 14/06 | Kyleakin | 11 - 3 | Portree | Kyleakin |
| 2019-06-15 14:30:00Sat 15/06 | Mallaig | 2 - 0 | Sleat & Strath | Mallaig |
| 2019-06-15 18:00:00Sat 15/06 | Portree Juniors | 8 - 4 | Kyle | Portree High School |
| 2019-06-15 18:00:00Sat 15/06 | GA United | 7 - 0 | Glenelg | Gairloch |
| 2019-06-22 14:30:00Sat 22/06 | Mallaig | 4 - 1 | Portree Juniors | Mallaig |
| 2019-06-22 18:00:00Sat 22/06 | GA United | 1 - 2 | NW Skye | Gairloch |
| 2019-06-28 19:30:00Fri 28/06 | Glenelg | 3 - 4 | Portree Juniors | Glenelg |
| 2019-06-29 18:00:00Sat 29/06 | Kyleakin | 2 - 2 | GA United | Kyleakin |
| 2019-06-29 18:00:00Sat 29/06 | Portree | 1 - 3 | Mallaig | Portree High School |
| 2019-07-02 19:15:00Tue 02/07 | NW Skye | 2 - 3 | Sleat & Strath | Uig |
| 2019-07-05 19:30:00Fri 05/07 | NW Skye | 4 - 1 | Kyleakin | Uig |
| 2019-07-06 12:00:00Sat 06/07 | GA United | 1 - 3 | Mallaig | Gairloch |
| 2019-07-06 18:00:00Sat 06/07 | Kyle | 0 - 7 | Glenelg | Kyle |
| 2019-07-10 19:15:00Wed 10/07 | Portree Juniors | 1 - 3 | Sleat & Strath | Portree High School |
| 2019-07-20 15:00:00Sat 20/07 | Mallaig | 3 - 0 | NW Skye | Mallaig |
| 2019-07-23 19:00:00Tue 23/07 | Sleat & Strath | 16 - 0 | Kyle | Broadford |
| 2019-07-24 19:15:00Wed 24/07 | Portree Juniors | 2 - 2 | Kyleakin | Portree High School |
| 2019-07-27 18:00:00Sat 27/07 | Portree | 3 - 3 | GA United | Portree High School |
| 2019-07-30 19:00:00Tue 30/07 | Sleat & Strath | 10 - 2 | Portree | Broadford |
| 2019-07-30 19:15:00Tue 30/07 | GA United | 2 - 0 | Kyle | Gairloch |
| 2019-07-31 19:00:00Wed 31/07 | Kyleakin | 2 - 1 | Glenelg | Kyleakin |
| 2019-07-31 19:30:00Wed 31/07 | Portree Juniors | 1 - 1 | NW Skye | Portree High School |
| 2019-08-03 13:00:00Sat 03/08 | Portree Juniors | 2 - 4 | Mallaig | Portree High School |
| 2019-08-03 18:00:00Sat 03/08 | NW Skye | 6 - 1 | GA United | Uig |
| 2019-08-06 19:00:00Tue 06/08 | Kyle | 3 - 5 | Kyleakin | Kyle |
| 2019-08-09 19:00:00Fri 09/08 | Sleat & Strath | 13 - 1 | Glenelg | Broadford |
| 2019-08-10 14:30:00Sat 10/08 | Mallaig | 8 - 0 | Kyle | Mallaig |
| 2019-08-10 18:00:00Sat 10/08 | Portree | 3 - 5 | NW Skye | Portree High School |
| 2019-08-10 18:00:00Sat 10/08 | GA United | 8 - 3 | Portree Juniors | Gairloch |
| 2019-08-21 18:45:00Wed 21/08 | Sleat & Strath | 11 - 0 | GA United | Broadford |
| 2019-08-21 18:45:00Wed 21/08 | Kyleakin | 3 - 1 | Mallaig | Kyleakin |
| 2019-08-24 14:30:00Sat 24/08 | Mallaig | 17 - 0 | Glenelg | Mallaig |
| 2019-08-24 18:00:00Sat 24/08 | NW Skye | 14 - 0 | Kyle | Uig |
| 2019-08-24 18:00:00Sat 24/08 | Kyleakin | 0 - 3 | Sleat & Strath | Kyleakin |
| 2019-08-28 18:45:00Wed 28/08 | Glenelg | 5 - 1 | Portree | Glenelg |
| 2019-08-31 13:30:00Sat 31/08 | Mallaig | 7 - 2 | Kyleakin | Mallaig |
| 2019-09-04 18:30:00Wed 04/09 | Glenelg | 1 - 4 | NW Skye | Glenelg |
| 2019-09-04 19:30:00Wed 04/09 | Portree Juniors | 2 - 1 | Portree | Portree High School |
| 2019-09-04 19:30:00Wed 04/09 | GA United | 3 - 7 | Sleat & Strath | Gairloch |
| 2019-09-07 12:00:00Sat 07/09 | Kyle | 4 - 3 | Portree Juniors | Kyle |
| 2019-09-07 14:00:00Sat 07/09 | Sleat & Strath | 2 - 5 | Mallaig | Broadford |
| 2019-09-07 17:00:00Sat 07/09 | Portree | 0 - 3 | Kyleakin | Portree High School |
| 2019-09-07 17:00:00Sat 07/09 | Glenelg | 4 - 2 | GA United | Glenelg |
| 2019-09-28 16:00:00Sat 28/09 | Kyle | 16:00:0016:00 | Portree | Kyle |
