| 2019-04-06 18:00:00Sat 06/04 | Portree Juniors | 8 - 0 | Glenelg | William Wilson League |
| 2019-04-27 18:00:00Sat 27/04 | Portree | 7 - 1 | Glenelg | William Wilson League |
| 2019-05-01 19:00:00Wed 01/05 | Glenelg | 4 - 2 | Kyle | 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 | Mallaig | 3 - 0 | Glenelg | GF MacRae Cup |
| 2019-05-28 19:00:00Tue 28/05 | Glenelg | 1 - 3 | Kyleakin | William Wilson League |
| 2019-05-31 19:00:00Fri 31/05 | Glenelg | 0 - 4 | Mallaig | William Wilson League |
| 2019-06-08 18:00:00Sat 08/06 | NW Skye | 5 - 0 | Glenelg | William Wilson League |
| 2019-06-15 18:00:00Sat 15/06 | GA United | 7 - 0 | Glenelg | William Wilson League |
| 2019-06-28 19:30:00Fri 28/06 | Glenelg | 3 - 4 | Portree Juniors | William Wilson League |
| 2019-07-06 18:00:00Sat 06/07 | Kyle | 0 - 7 | Glenelg | William Wilson League |
| 2019-07-12 19:00:00Fri 12/07 | NW Skye | 12 - 0 | Glenelg | Ross Cup |
| 2019-07-31 19:00:00Wed 31/07 | Kyleakin | 2 - 1 | Glenelg | William Wilson League |
| 2019-08-09 19:00:00Fri 09/08 | Sleat & Strath | 13 - 1 | Glenelg | William Wilson League |
| 2019-08-24 14:30:00Sat 24/08 | Mallaig | 17 - 0 | Glenelg | William Wilson League |
| 2019-08-28 18:45:00Wed 28/08 | Glenelg | 5 - 1 | Portree | William Wilson League |
| 2019-09-04 18:30:00Wed 04/09 | Glenelg | 1 - 4 | NW Skye | William Wilson League |
| 2019-09-07 17:00:00Sat 07/09 | Glenelg | 4 - 2 | GA United | William Wilson League |
| 2019-09-21 17:00:00Sat 21/09 | Portree Juniors | 2 - 3 | Glenelg | Clan Donald Cup |
| 2019-09-28 12:00:00Sat 28/09 | Glenelg | 2 - 1 | GA United | Clan Donald Cup |
