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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.
| Tournament details | |
|---|---|
| Country |  Scotland |
| Teams | 16 |
| Final positions | |
| Champions | Forres Mechanics |
| Runner-up | Keith |
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.
District 1
| Pos | Team | Pld | W | D | L | GF | GA | GD | Pts |
|---|---|---|---|---|---|---|---|---|---|
| 1 | Keith | 3 | 2 | 1 | 0 | 4 | 1 | +3 | 7 |
| 2 | Peterhead | 3 | 2 | 0 | 1 | 5 | 4 | +1 | 6 |
| 3 | Fraserburgh | 3 | 1 | 0 | 2 | 8 | 5 | +3 | 3 |
| 4 | Rothes | 3 | 0 | 1 | 2 | 2 | 9 | −7 | 1 |
District 2
| Pos | Team | Pld | W | D | L | GF | GA | GD | Pts |
|---|---|---|---|---|---|---|---|---|---|
| 1 | Huntly | 3 | 2 | 1 | 0 | 5 | 0 | +5 | 7 |
| 2 | Cove Rangers | 3 | 2 | 0 | 1 | 4 | 5 | −1 | 6 |
| 3 | Buckie Thistle | 3 | 1 | 0 | 2 | 3 | 5 | −2 | 3 |
| 4 | Deveronvale | 3 | 0 | 1 | 2 | 2 | 4 | −2 | 1 |
District 3
| Pos | Team | Pld | W | D | L | GF | GA | GD | Pts |
|---|---|---|---|---|---|---|---|---|---|
| 1 | Forres Mechanics | 3 | 2 | 1 | 0 | 8 | 3 | +5 | 7 |
| 2 | Lossiemouth | 3 | 2 | 1 | 0 | 5 | 1 | +4 | 7 |
| 3 | Nairn County | 3 | 1 | 0 | 2 | 4 | 9 | −5 | 3 |
| 4 | Elgin City | 3 | 0 | 0 | 3 | 1 | 5 | −4 | 0 |
District 4
| Pos | Team | Pld | W | D | L | GF | GA | GD | Pts |
|---|---|---|---|---|---|---|---|---|---|
| 1 | Brora Rangers | 3 | 3 | 0 | 0 | 5 | 1 | +4 | 9 |
| 2 | Clachnacuddin | 3 | 2 | 0 | 1 | 8 | 1 | +7 | 6 |
| 3 | Fort William | 3 | 0 | 1 | 2 | 3 | 6 | −3 | 1 |
| 4 | Wick Academy | 3 | 0 | 1 | 2 | 2 | 10 | −8 | 1 |
Ties in the semi-finals took place on Saturday 1 May
| Home team | Score | Away team |
|---|---|---|
| Brora Rangers | 0-1 | Keith |
| Forres Mechanics | 2-1 | Huntly |
| Forres Mechanics | 1-0 | Keith |
|---|---|---|
| Bavidge |
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