| 2019-04-27 14:00:21Sat 27/04 | GA United | 2 - 3 | Maryburgh | Gairloch |
| 2019-04-27 15:00:28Sat 27/04 | Police | 2 - 1 | Portree Juniors | Bught Park, Inverness |
| 2019-04-27 15:00:53Sat 27/04 | Tomatin | 1 - 2 | Mallaig | Bught Park, Inverness |
| 2019-05-18 14:00:20Sat 18/05 | Mallaig | 2 - 4 | Balloan Compass | Mallaig |
| 2019-05-18 15:00:08Sat 18/05 | Fortrose & Rosemarkie Union | 4 - 7 | Sleat & Strath | Fortrose |
| 2019-05-18 15:00:34Sat 18/05 | NW Skye | 0 - 2 | Hill Rovers | Uig |
| 2019-05-18 15:00:45Sat 18/05 | Innes CI | 2 - 4 | Kyleakin | Bught Park, Inverness |
| 2019-06-08 15:00:45Sat 08/06 | Stornoway Athletic | 15:00:4515:00 | Kyleakin | Stornoway |
| 2019-06-08 15:00:58Sat 08/06 | Sleat & Strath | 15:00:5815:00 | Balloan Compass | Broadford |
