| 2019-04-06 18:00:00Sat 06/04 | Portree Juniors | 8 - 0 | Glenelg | William Wilson League |
| 2019-04-20 18:00:00Sat 20/04 | Kyleakin | 1 - 1 | Portree Juniors | William Wilson League |
| 2019-04-27 15:00:28Sat 27/04 | Police | 2 - 1 | Portree Juniors | Highland Amateur Cup |
| 2019-05-01 19:15:00Wed 01/05 | Sleat & Strath | 3 - 2 | Portree Juniors | William Wilson League |
| 2019-05-11 18:00:00Sat 11/05 | Sleat & Strath | 7 - 1 | Portree Juniors | GF MacRae Cup |
| 2019-05-18 14:00:00Sat 18/05 | Portree Juniors | 1 - 3 | GA United | William Wilson League |
| 2019-05-28 19:15:00Tue 28/05 | NW Skye | 2 - 1 | Portree Juniors | William Wilson League |
| 2019-06-05 19:30:00Wed 05/06 | Portree | 3 - 2 | Portree Juniors | William Wilson League |
| 2019-06-15 18:00:00Sat 15/06 | Portree Juniors | 8 - 4 | Kyle | William Wilson League |
| 2019-06-22 14:30:00Sat 22/06 | Mallaig | 4 - 1 | Portree Juniors | William Wilson League |
| 2019-06-28 19:30:00Fri 28/06 | Glenelg | 3 - 4 | Portree Juniors | William Wilson League |
| 2019-07-10 19:15:00Wed 10/07 | Portree Juniors | 1 - 3 | Sleat & Strath | William Wilson League |
| 2019-07-20 18:00:00Sat 20/07 | Portree Juniors | 18:00:0018:00 | GA United | Ross Cup |
| 2019-07-24 19:15:00Wed 24/07 | Portree Juniors | 19:15:0019:15 | Kyleakin | William Wilson League |
| 2019-07-31 19:30:00Wed 31/07 | Portree Juniors | 19:30:0019:30 | NW Skye | William Wilson League |
| 2019-08-03 18:00:00Sat 03/08 | Portree Juniors | 18:00:0018:00 | Mallaig | William Wilson League |
| 2019-08-10 18:00:00Sat 10/08 | GA United | 18:00:0018:00 | Portree Juniors | William Wilson League |
| 2019-08-21 19:30:00Wed 21/08 | Portree Juniors | 19:30:0019:30 | Portree | William Wilson League |
| 2019-09-07 17:00:00Sat 07/09 | Kyle | 17:00:0017:00 | Portree Juniors | William Wilson League |
