| 2019-04-06 15:00:00Sat 06/04 | GA United | 3 - 4 | Kyleakin | William Wilson League |
| 2019-04-13 18:00:00Sat 13/04 | Kyleakin | 3 - 1 | NW Skye | William Wilson League |
| 2019-04-20 18:00:00Sat 20/04 | Kyleakin | 1 - 1 | Portree Juniors | William Wilson League |
| 2019-04-27 18:00:00Sat 27/04 | Kyleakin | 6 - 2 | Kyle | William Wilson League |
| 2019-05-18 15:00:45Sat 18/05 | Innes CI | 2 - 4 | Kyleakin | Highland Amateur Cup |
| 2019-05-21 19:00:00Tue 21/05 | Kyleakin | 10 - 1 | GA United | GF MacRae Cup |
| 2019-05-25 14:30:00Sat 25/05 | Mallaig | 3 - 5 | Kyleakin | GF MacRae Cup |
| 2019-05-28 19:00:00Tue 28/05 | Glenelg | 1 - 3 | Kyleakin | William Wilson League |
| 2019-06-01 18:00:00Sat 01/06 | Sleat & Strath | 6 - 2 | Kyleakin | William Wilson League |
| 2019-06-08 15:00:45Sat 08/06 | Stornoway Athletic | 2 - 0 | Kyleakin | Highland Amateur Cup |
| 2019-06-14 19:30:00Fri 14/06 | Kyleakin | 11 - 3 | Portree | William Wilson League |
| 2019-06-22 18:00:00Sat 22/06 | Kyleakin | 0 - 7 | Sleat & Strath | GF MacRae Cup |
| 2019-06-29 18:00:00Sat 29/06 | Kyleakin | 2 - 2 | GA United | William Wilson League |
| 2019-07-05 19:30:00Fri 05/07 | NW Skye | 4 - 1 | Kyleakin | William Wilson League |
| 2019-07-13 18:00:00Sat 13/07 | Portree | 0 - 2 | Kyleakin | Ross Cup |
| 2019-07-24 19:15:00Wed 24/07 | Portree Juniors | 19:15:0019:15 | Kyleakin | William Wilson League |
| 2019-07-27 18:00:00Sat 27/07 | Kyleakin | 18:00:0018:00 | Mallaig | William Wilson League |
| 2019-07-31 19:00:00Wed 31/07 | Kyleakin | 19:00:0019:00 | Glenelg | William Wilson League |
| 2019-08-02 19:00:00Fri 02/08 | Kyle | 19:00:0019:00 | Kyleakin | William Wilson League |
| 2019-08-24 18:00:00Sat 24/08 | Kyleakin | 18:00:0018:00 | Sleat & Strath | William Wilson League |
| 2019-08-31 18:00:00Sat 31/08 | Mallaig | 18:00:0018:00 | Kyleakin | William Wilson League |
| 2019-09-07 17:00:00Sat 07/09 | Portree | 17:00:0017:00 | Kyleakin | William Wilson League |
