1998–99 Highland League Cup
| Tournament details | |
|---|---|
| Country | Scotland |
| Teams | 16 |
| Final positions | |
| Champions | Forres Mechanics |
| Runners-up | Keith |
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.