| 2019-04-06 13:30:00Sat 06/04 | Mallaig | 3 - 0 | Portree | William Wilson League |
| 2019-04-20 17:00:00Sat 20/04 | GA United | 1 - 2 | Portree | William Wilson League |
| 2019-04-27 18:00:00Sat 27/04 | Portree | 7 - 1 | Glenelg | William Wilson League |
| 2019-05-03 19:00:00Fri 03/05 | NW Skye | 3 - 3 | Portree | William Wilson League |
| 2019-05-11 18:00:00Sat 11/05 | Portree | 1 - 6 | NW Skye | GF MacRae Cup |
| 2019-05-24 19:15:00Fri 24/05 | Portree | 8 - 2 | Kyle | William Wilson League |
| 2019-05-28 19:30:00Tue 28/05 | Portree | 1 - 6 | Sleat & Strath | William Wilson League |
| 2019-06-05 19:30:00Wed 05/06 | Portree | 3 - 2 | Portree Juniors | William Wilson League |
| 2019-06-14 19:30:00Fri 14/06 | Kyleakin | 11 - 3 | Portree | William Wilson League |
| 2019-06-29 18:00:00Sat 29/06 | Portree | 1 - 3 | Mallaig | William Wilson League |
| 2019-07-13 18:00:00Sat 13/07 | Portree | 0 - 2 | Kyleakin | Ross Cup |
| 2019-07-27 18:00:00Sat 27/07 | Portree | 3 - 3 | GA United | William Wilson League |
| 2019-07-30 19:00:00Tue 30/07 | Sleat & Strath | 10 - 2 | Portree | William Wilson League |
| 2019-08-10 18:00:00Sat 10/08 | Portree | 3 - 5 | NW Skye | William Wilson League |
| 2019-08-28 18:45:00Wed 28/08 | Glenelg | 5 - 1 | Portree | William Wilson League |
| 2019-09-04 19:30:00Wed 04/09 | Portree Juniors | 2 - 1 | Portree | William Wilson League |
| 2019-09-07 17:00:00Sat 07/09 | Portree | 0 - 3 | Kyleakin | William Wilson League |
| 2019-09-18 19:00:00Wed 18/09 | Portree Juniors | 2 - 0 | Portree | Clan Donald Cup |
| 2019-09-28 16:00:00Sat 28/09 | Kyle | 16:00:0016:00 | Portree | William Wilson League |
