1998–99 Highland League Cup

The 1998–99 Tennents Highland League Cup was the 54th edition of the Highland League's premier knock-out football competition. The winners were Forres Mechanics, who defeated Keith 1-0 in the final at Borough Briggs in Elgin.

Group stage
The first stage of the Cup was a group stage consisting of four groups, called districts, of four teams. The four group winners qualified for the semi-finals.

Semi-finals
Ties in the semi-finals took place on Saturday 1 May