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 is used to whittle the number of clubs down to sixteen for the First Round. Formartine United are defending the trophy this season.
2018-19 COMPETITION (2016-17, 2017-18)
Preliminary Round (Nov 3)
- Clachnacuddin 0-5 Brora Rangers
- Nairn County 1-3 Buckie Thistle
First Round (Nov 17)
- Cove Rangers 8-0 Turriff United
- Fort William 0-3 Wick Academy
- Formartine United 5-2 Inverurie Loco Works
- Fraserburgh 1-2 Deveronvale
- Keith 2-5 Brora Rangers
- Lossiemouth 0-4 Huntly
- Rothes 0-2 Buckie Thistle
- Strathspey Thistle 2-5 Forres Mechanics
Second Round (Dec 8)
- Wick Academy 1-0 Forres Mechanics (Dec 7)
- Buckie Thistle 1-3 Brora Rangers
- Cove Rangers 5-0 Huntly
- Formartine United 4-1 Deveronvale
Semi Finals (Mar 16)
- Brora Rangers 0-2 Formartine United
- Cove Rangers 3-1 Wick Academy
Final (Apr 6)
- Cove Rangers 2-0 Formartine United (@ Harlaw Park, Inverurie)