The Highland League Cup is contested by all eighteen members of the Highland Football League in a straight knockout format.
A preliminary round of two ties will be used to whittle the number of clubs down to sixteen for the First Round. Brechin City are making their first appearance in this competition this season.
Rothes are the current holders having won the last final which was the 2019-20 edition, played belatedly in October 2020.
Preliminary Round (Oct 30)
- Deveronvale 1-1(4-3p) Lossiemouth
- Fort William 1-10 Brora Rangers (Nov 3 @ Dudgeon Park, post Oct 30)
First Round (Nov 13)
- Buckie Thistle 3-0 Nairn County
- Clachnacuddin 1-0 Strathspey Thistle
- Deveronvale 2-4 Rothes
- Formartine United 0-1 Brechin City
- Forres Mechanics 2-1 Turriff United
- Keith 1-4 Fraserburgh
- Inverurie Loco Works 1-0 Huntly
- Wick Academy 0-3 Brora Rangers
- Brechin City 0-2 Brora Rangers (Feb 23, post Dec 4)
- Buckie Thistle 1-0 Inverurie Loco Works (Mar 2, post Dec 4, Feb 23)
- Forres Mechanics 2-1 Clachnacuddin (Mar 2, post Dec 4, Feb 23)
- Rothes 1-2 Fraserburgh (Mar 2, post Dec 4, Feb 23)
- Forres Mechanics 0-2 Buckie Thistle (Mar 12)
- Fraserburgh 1-1(2-4p) Brora Rangers (Mar 12)
- Buckie Thistle 1-2 Brora Rangers (Apr 9 @ Station Park, Nairn)