| 2023-04-07 18:15:00Fri 07/04 | Kyleakin | 1 - 2 | Sleat & Strath | William Wilson League | N/A |
| 2023-04-08 14:00:00Sat 08/04 | Portree Juniors | 0 - 0 | North West Skye | William Wilson League | N/A |
| 2023-04-08 14:00:00Sat 08/04 | Mallaig | 3 - 0 | Kyle | William Wilson League | N/A |
| 2023-04-14 18:30:00Fri 14/04 | Kyleakin | 5 - 2 | Portree Juniors | William Wilson League | N/A |
| 2023-04-15 14:15:00Sat 15/04 | Portree | 0 - 2 | Mallaig | William Wilson League | N/A |
| 2023-04-15 15:00:00Sat 15/04 | North West Skye | 8 - 2 | Fort William | William Wilson League | N/A |
| 2023-04-21 18:30:40Fri 21/04 | Fort William | 2 - 5 | Portree | Highland Amateur Cup | N/A |
| 2023-04-22 14:00:24Sat 22/04 | Clach | 3 - 1 | Kyleakin | Highland Amateur Cup | N/A |
| 2023-04-22 14:00:49Sat 22/04 | Highland | 0 - 5 | Sleat & Strath | Highland Amateur Cup | N/A |
| 2023-04-22 14:00:52Sat 22/04 | North West Skye | 7 - 3 | Tomatin | Highland Amateur Cup | N/A |
| 2023-04-25 19:00:00Tue 25/04 | Portree | 2 - 5 | North West Skye | William Wilson League | N/A |
| 2023-04-25 19:00:00Tue 25/04 | Portree Juniors | 2 - 5 | Sleat & Strath | William Wilson League | N/A |
| 2023-04-28 18:30:00Fri 28/04 | Kyle | 0 - 6 | North West Skye | GF MacRae Cup | N/A |
| 2023-04-29 14:00:00Sat 29/04 | Portree Juniors | 1 - 4 | Kyleakin | GF MacRae Cup | N/A |
| 2023-04-29 14:15:00Sat 29/04 | Portree | 2 - 5 | Mallaig | GF MacRae Cup | N/A |
| 2023-04-29 15:00:00Sat 29/04 | Sleat & Strath | 6 - 2 | Fort William | GF MacRae Cup | N/A |
| 2023-05-02 19:00:00Tue 02/05 | Sleat & Strath | 5 - 1 | Kyle | William Wilson League | N/A |
| 2023-05-03 19:00:00Wed 03/05 | Fort William | 2 - 8 | Mallaig | William Wilson League | N/A |
| 2023-05-05 19:00:00Fri 05/05 | Kyle | 1 - 3 | Portree Juniors | William Wilson League | N/A |
| 2023-05-05 19:00:00Fri 05/05 | North West Skye | 1 - 2 | Sleat & Strath | William Wilson League | N/A |
| 2023-05-05 19:00:00Fri 05/05 | Kyleakin | 1 - 1 | Portree | William Wilson League | N/A |
| 2023-05-12 19:30:00Fri 12/05 | Kyle | 0 - 5 | Fort William | William Wilson League | N/A |
| 2023-05-13 14:00:09Sat 13/05 | Ferrybache | 5 - 4 | Sleat & Strath | Highland Amateur Cup | N/A |
| 2023-05-13 14:00:18Sat 13/05 | Black Rock Rovers | 5 - 2 | Portree | Highland Amateur Cup | N/A |
| 2023-05-13 14:00:44Sat 13/05 | Auctioneers | 0 - 3 | Mallaig | Highland Amateur Cup | N/A |
| 2023-05-13 15:00:25Sat 13/05 | North West Skye | 7 - 1 | Glen Urquhart | Highland Amateur Cup | N/A |
| 2023-05-19 18:30:00Fri 19/05 | Kyleakin | 2 - 3 | North West Skye | GF MacRae Cup | N/A |
| 2023-05-20 12:00:00Sat 20/05 | Sleat & Strath | 1 - 4 | Mallaig | GF MacRae Cup | N/A |
| 2023-05-20 15:00:00Sat 20/05 | Portree | 7 - 2 | Fort William | William Wilson League | N/A |
| 2023-05-25 19:30:00Thu 25/05 | Kyleakin | 7 - 2 | Kyle | William Wilson League | N/A |
| 2023-05-26 19:00:00Fri 26/05 | Sleat & Strath | 6 - 0 | Portree | William Wilson League | N/A |
| 2023-05-27 12:30:00Sat 27/05 | Mallaig | 1 - 4 | North West Skye | William Wilson League | N/A |
| 2023-06-02 19:00:00Fri 02/06 | Kyle | 1 - 4 | Portree | William Wilson League | N/A |
| 2023-06-02 19:30:00Fri 02/06 | Sleat & Strath | 4 - 3 | Fort William | William Wilson League | N/A |
| 2023-06-03 13:00:47Sat 03/06 | Mallaig | 2 - 1 | North West Skye | Highland Amateur Cup | N/A |
| 2023-06-06 19:30:00Tue 06/06 | North West Skye | 2 - 0 | Kyleakin | William Wilson League | N/A |
| 2023-06-09 19:00:00Fri 09/06 | Kyle | 1 - 7 | North West Skye | William Wilson League | N/A |
| 2023-06-09 19:00:00Fri 09/06 | Portree | 1 - 4 | Portree Juniors | William Wilson League | N/A |
| 2023-06-10 15:00:00Sat 10/06 | Fort William | 3 - 0 | Kyleakin | William Wilson League | N/A |
| 2023-06-17 13:00:00Sat 17/06 | Mallaig | 0 - 5 | North West Skye | GF MacRae Cup | N/A |
| 2023-06-17 14:00:00Sat 17/06 | Portree Juniors | 2 - 1 | Fort William | William Wilson League | N/A |
| 2023-06-23 19:00:25Fri 23/06 | Kyle | 3 - 9 | Sleat & Strath | William Wilson League | N/A |
| 2023-06-24 13:00:03Sat 24/06 | Mallaig | 2 - 4 | Loch Ness | Highland Amateur Cup | N/A |
| 2023-06-24 14:00:00Sat 24/06 | Portree Juniors | 3 - 0 | Kyleakin | William Wilson League | N/A |
| 2023-06-24 15:00:00Sat 24/06 | Fort William | 0 - 5 | North West Skye | William Wilson League | N/A |
| 2023-06-30 19:00:00Fri 30/06 | Sleat & Strath | 3 - 2 | 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 |
| 2023-07-01 13:30:00Sat 01/07 | Kyleakin | 1 - 4 | Mallaig | William Wilson League | N/A |
| 2023-07-01 15:00:00Sat 01/07 | Fort William | 8 - 0 | Kyle | William Wilson League | N/A |
| 2023-07-04 19:00:00Tue 04/07 | Portree Juniors | 2 - 0 | Kyle | William Wilson League | N/A |
| 2023-07-04 19:00:00Tue 04/07 | Portree | 2 - 4 | Kyleakin | William Wilson League | N/A |
| 2023-07-04 19:30:00Tue 04/07 | Mallaig | 5 - 1 | Fort William | William Wilson League | N/A |
| 2023-07-07 19:00:00Fri 07/07 | Sleat & Strath | 3 - 1 | North West Skye | William Wilson League | N/A |
| 2023-07-14 19:00:00Fri 14/07 | Portree | 1 - 5 | Kyleakin | Ross Cup | N/A |
| 2023-07-15 13:30:00Sat 15/07 | North West Skye | 4 - 7 | Mallaig | Ross Cup | N/A |
| 2023-07-15 14:00:00Sat 15/07 | Portree Juniors | 5 - 1 | Kyle | Ross Cup | N/A |
| 2023-07-21 19:00:00Fri 21/07 | Portree | 1 - 5 | Sleat & Strath | William Wilson League | N/A |
| 2023-07-21 19:00:00Fri 21/07 | Kyle | 2 - 7 | Kyleakin | William Wilson League | N/A |
| 2023-07-22 13:45:00Sat 22/07 | North West Skye | 1 - 1 | Mallaig | William Wilson League | N/A |
| 2023-07-22 15:00:00Sat 22/07 | Fort William | 0 - 1 | Portree Juniors | William Wilson League | N/A |
| 2023-07-25 18:45:00Tue 25/07 | Fort William | 2 - 1 | Sleat & Strath | Ross Cup | N/A |
| 2023-07-29 12:00:00Sat 29/07 | Mallaig | 4 - 1 | Kyleakin | William Wilson League | N/A |
| 2023-08-01 19:00:00Tue 01/08 | Mallaig | 1 - 1 | Fort William | Ross Cup | N/A |
| 2023-08-01 19:15:00Tue 01/08 | Kyleakin | 4 - 3 | Portree Juniors | Ross Cup | N/A |
| 2023-08-04 19:00:00Fri 04/08 | Kyleakin | 1 - 6 | North West Skye | William Wilson League | N/A |
| 2023-08-04 19:00:00Fri 04/08 | Portree | 3 - 0 | Kyle | William Wilson League | N/A |
| 2023-08-05 12:00:00Sat 05/08 | Mallaig | 3 - 2 | Portree Juniors | William Wilson League | N/A |
| 2023-08-05 18:00:00Sat 05/08 | Fort William | 5 - 6 | Sleat & Strath | William Wilson League | N/A |
| 2023-08-12 12:00:00Sat 12/08 | Portree Juniors | 1 - 5 | Mallaig | William Wilson League | N/A |
| 2023-08-12 13:00:00Sat 12/08 | Fort William | 5 - 3 | Portree | William Wilson League | N/A |
| 2023-08-18 19:00:00Fri 18/08 | North West Skye | 1 - 2 | Kyle | William Wilson League | N/A |
| 2023-08-19 12:00:00Sat 19/08 | Mallaig | 2 - 1 | Sleat & Strath | William Wilson League | N/A |
| 2023-08-19 14:00:00Sat 19/08 | Portree Juniors | 2 - 2 | Portree | William Wilson League | N/A |
| 2023-08-19 15:00:00Sat 19/08 | Kyleakin | 8 - 4 | Fort William | William Wilson League | N/A |
| 2023-08-25 19:00:00Fri 25/08 | North West Skye | 5 - 2 | Portree Juniors | William Wilson League | N/A |
| 2023-08-25 19:15:00Fri 25/08 | Sleat & Strath | 3 - 1 | Kyleakin | William Wilson League | N/A |
| 2023-08-26 14:00:00Sat 26/08 | Kyle | 0 - 7 | Mallaig | William Wilson League | N/A |
| 2023-08-29 19:00:00Tue 29/08 | Kyle | 1 - 5 | Portree | Clan Donald Cup | N/A |
| 2023-09-01 18:30:00Fri 01/09 | Sleat & Strath | 3 - 6 | North West Skye | Ewen MacRae Cup | N/A |
| 2023-09-02 10:30:00Sat 02/09 | Mallaig | 3 - 0 | Portree | William Wilson League | N/A |
| 2023-09-02 15:00:00Sat 02/09 | Fort William | 0 - 3 | Kyleakin | Clan Donald Cup | N/A |
| 2023-09-08 18:30:00Fri 08/09 | Kyleakin | 9 - 1 | Portree | Clan Donald Cup | N/A |
| 2023-09-09 14:00:00Sat 09/09 | Sleat & Strath | 2 - 3 | Mallaig | William Wilson League | N/A |
| 2023-09-16 13:30:00Sat 16/09 | Mallaig | 8 - 6 | Kyleakin | Ross Cup | N/A |
| 2023-09-23 13:30:00Sat 23/09 | Portree Juniors | 0 - 1 | Mallaig | Ewen MacRae Cup | N/A |
| 2023-09-30 13:30:00Sat 30/09 | North West Skye | 6 - 1 | Mallaig | Ewen MacRae Cup | N/A |
