| 2023-04-15 14:15:00Sat 15/04 | Portree | 0 - 2 | Mallaig | William Wilson League | N/A |
| 2023-04-21 18:30:40Fri 21/04 | Fort William | 2 - 5 | Portree | Highland Amateur Cup | N/A |
| 2023-04-25 19:00:00Tue 25/04 | Portree | 2 - 5 | North West Skye | William Wilson League | N/A |
| 2023-04-29 14:15:00Sat 29/04 | Portree | 2 - 5 | Mallaig | GF MacRae Cup | N/A |
| 2023-05-05 19:00:00Fri 05/05 | Kyleakin | 1 - 1 | Portree | William Wilson League | N/A |
| 2023-05-13 14:00:18Sat 13/05 | Black Rock Rovers | 5 - 2 | Portree | Highland Amateur Cup | N/A |
| 2023-05-20 15:00:00Sat 20/05 | Portree | 7 - 2 | Fort William | William Wilson League | N/A |
| 2023-05-26 19:00:00Fri 26/05 | Sleat & Strath | 6 - 0 | Portree | William Wilson League | N/A |
| 2023-06-02 19:00:00Fri 02/06 | Kyle | 1 - 4 | Portree | William Wilson League | N/A |
| 2023-06-09 19:00:00Fri 09/06 | Portree | 1 - 4 | Portree Juniors | William Wilson League | N/A |
| 2023-06-30 19:00:00Fri 30/06 | North West Skye | 4 - 1 | Portree | William Wilson League | N/A |
| 2023-07-04 19:00:00Tue 04/07 | Portree | 2 - 4 | Kyleakin | William Wilson League | N/A |
| 2023-07-14 19:00:00Fri 14/07 | Portree | 1 - 5 | Kyleakin | Ross Cup | N/A |
| 2023-07-21 19:00:00Fri 21/07 | Portree | 1 - 5 | Sleat & Strath | William Wilson League | N/A |
| 2023-08-04 19:00:00Fri 04/08 | Portree | 3 - 0 | Kyle | William Wilson League | N/A |
| 2023-08-12 13:00:00Sat 12/08 | Fort William | 5 - 3 | Portree | William Wilson League | N/A |
| 2023-08-19 14:00:00Sat 19/08 | Portree Juniors | 2 - 2 | Portree | William Wilson League | N/A |
| 2023-08-29 19:00:00Tue 29/08 | Kyle | 1 - 5 | Portree | Clan Donald Cup | N/A |
| 2023-09-02 10:30:00Sat 02/09 | Mallaig | 3 - 0 | Portree | William Wilson League | N/A |
| 2023-09-08 18:30:00Fri 08/09 | Kyleakin | 9 - 1 | Portree | Clan Donald Cup | N/A |
