| 2019-04-06 18:00:00Sat 06/04 | Sleat & Strath | 3 - 1 | NW Skye | William Wilson League |
| 2019-04-19 18:45:00Fri 19/04 | Kyle | 1 - 8 | Sleat & Strath | William Wilson League |
| 2019-05-01 19:15:00Wed 01/05 | Sleat & Strath | 3 - 2 | Portree Juniors | William Wilson League |
| 2019-05-04 18:00:00Sat 04/05 | Glenelg | 0 - 12 | Sleat & Strath | William Wilson League |
| 2019-05-11 18:00:00Sat 11/05 | Sleat & Strath | 7 - 1 | Portree Juniors | GF MacRae Cup |
| 2019-05-18 15:00:08Sat 18/05 | Fortrose & Rosemarkie Union | 4 - 7 | Sleat & Strath | Highland Amateur Cup |
| 2019-05-25 18:00:00Sat 25/05 | Sleat & Strath | 3 - 2 | NW Skye | GF MacRae Cup |
| 2019-05-28 19:30:00Tue 28/05 | Portree | 1 - 6 | Sleat & Strath | William Wilson League |
| 2019-06-01 18:00:00Sat 01/06 | Sleat & Strath | 6 - 2 | Kyleakin | William Wilson League |
| 2019-06-08 13:00:58Sat 08/06 | Sleat & Strath | 3 - 0 | Balloan Compass | Highland Amateur Cup |
| 2019-06-15 14:30:00Sat 15/06 | Mallaig | 2 - 0 | Sleat & Strath | William Wilson League |
| 2019-06-22 18:00:00Sat 22/06 | Kyleakin | 0 - 7 | Sleat & Strath | GF MacRae Cup |
| 2019-06-29 15:00:02Sat 29/06 | Stornoway Athletic | 1 - 2 | Sleat & Strath | Highland Amateur Cup |
| 2019-07-02 19:15:00Tue 02/07 | NW Skye | 2 - 3 | Sleat & Strath | William Wilson League |
| 2019-07-10 19:15:00Wed 10/07 | Portree Juniors | 1 - 3 | Sleat & Strath | William Wilson League |
| 2019-07-13 14:30:00Sat 13/07 | Sleat & Strath | 5 - 1 | Mallaig | Ross Cup |
| 2019-07-20 15:00:07Sat 20/07 | Avoch | 2 - 1 | Sleat & Strath | Highland Amateur Cup |
| 2019-07-23 19:00:00Tue 23/07 | Sleat & Strath | 16 - 0 | Kyle | William Wilson League |
| 2019-07-27 18:00:00Sat 27/07 | Sleat & Strath | 4 - 4 | NW Skye | Ross Cup |
| 2019-07-30 19:00:00Tue 30/07 | Sleat & Strath | 10 - 2 | Portree | William Wilson League |
| 2019-08-09 19:00:00Fri 09/08 | Sleat & Strath | 13 - 1 | Glenelg | William Wilson League |
| 2019-08-21 18:45:00Wed 21/08 | Sleat & Strath | 18:45:0018:45 | GA United | William Wilson League |
| 2019-08-24 18:00:00Sat 24/08 | Kyleakin | 18:00:0018:00 | Sleat & Strath | William Wilson League |
| 2019-08-31 17:00:00Sat 31/08 | GA United | 17:00:0017:00 | Sleat & Strath | William Wilson League |
| 2019-09-07 15:00:00Sat 07/09 | Sleat & Strath | 15:00:0015:00 | Mallaig | William Wilson League |
| 2019-09-14 16:30:49Sat 14/09 | Sleat & Strath | 16:30:4916:30 | Kyleakin | Ross Cup |
