| Football League - Highland League | Buckie Thistle | Away | 01‑Aug 15:00 | |
| Football League - Highland League | Inverurie Loco Works | Home | 05‑Aug 20:00 | |
| Football League - Highland League | Strathspey Thistle | Home | 08‑Aug 15:00 | |
| Challenge Cup | Peterhead | Home | 11‑Aug 19:45 | |
| Football League - Highland League | Brora Rangers | Away | 15‑Aug 15:00 | |
| Football League - Highland League | Turriff United | Home | 19‑Aug 20:00 | |
| Football League - Highland League | Huntly | Away | 22‑Aug 15:00 | |
| Challenge Cup | Ross County | Away | 25‑Aug 19:45 | |
| Football League - Highland League | Invergordon | Home | 29‑Aug 15:00 | |
| Football League - Highland League | Rothes | Away | 05‑Sep 15:00 | |
| Challenge Cup | Forfar Athletic | Home | 08‑Sep 19:45 | |
| Football League - Highland League | Nairn County | Away | 12‑Sep 15:00 | |
| Football League - Highland League | Keith | Home | 16‑Sep 20:00 | |
| Football League - Highland League | Forres Mechanics | Away | 19‑Sep 15:00 | |
| Challenge Cup | Aberdeen U21 | Home | 22‑Sep 19:45 | |
| Challenge Cup | Dumbarton | Away | 26‑Sep 15:00 | |
| Football League - Highland League | Fraserburgh | Home | 07‑Oct 20:00 | |
| Football League - Highland League | Lossiemouth | Away | 10‑Oct 15:00 | |
| Challenge Cup | Motherwell U21 | Home | 13‑Oct 19:45 | |
| Football League - Highland League | Clachnacuddin | Home | 17‑Oct 15:00 | |
| Football League - Highland League | Deveronvale | Away | 31‑Oct 15:00 | |
| Football League - Highland League | Formartine United | Home | 14‑Nov 15:00 | |
| Football League - Highland League | Wick Academy | Away | 21‑Nov 15:00 | |
| Football League - Highland League | Buckie Thistle | Home | 05‑Dec 15:00 | |
| Football League - Highland League | Inverurie Loco Works | Away | 19‑Dec 15:00 | |
| Football League - Highland League | Strathspey Thistle | Away | 26‑Dec 15:00 | |
| Football League - Highland League | Brora Rangers | Home | 02‑Jan 15:00 | |
| Football League - Highland League | Turriff United | Away | 09‑Jan 15:00 | |
| Football League - Highland League | Huntly | Home | 16‑Jan 15:00 | |
| Football League - Highland League | Invergordon | Away | 23‑Jan 15:00 | |
| Football League - Highland League | Rothes | Home | 30‑Jan 15:00 | |
| Football League - Highland League | Keith | Away | 06‑Feb 15:00 | |
| Football League - Highland League | Forres Mechanics | Home | 20‑Feb 15:00 | |
| Football League - Highland League | Nairn County | Home | 27‑Feb 15:00 | |
| Football League - Highland League | Fraserburgh | Away | 06‑Mar 15:00 | |
| Football League - Highland League | Lossiemouth | Home | 13‑Mar 15:00 | |
| Football League - Highland League | Clachnacuddin | Away | 20‑Mar 15:00 | |
| Football League - Highland League | Deveronvale | Home | 03‑Apr 15:00 | |
| Football League - Highland League | Formartine United | Away | 10‑Apr 15:00 | |
