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The 1998–1999 Scottish League Cup was the 53rd staging of the Scotland's second most prestigious football knockout competition. The competition was won by Rangers, who defeated St Johnstone 2–1 in the Final. The Final was played at Celtic Park because Hampden Park was being redeveloped, work which was completed in time for the 1999 Scottish Cup Final.
| Tournament details | |
|---|---|
| Country | Scotland |
| Final positions | |
| Champions | Rangers |
| Runner-up | St Johnstone |
This was the last season in which the competition was completed in the autumn, which meant that there was no League Cup Final held in the calendar year of 1999. The next Final to be played was the 1999–2000 Final, which was played in March 2000.
| Home team | Score | Away team |
|---|---|---|
| Arbroath | 0–1 | Clydebank |
| Brechin City | 2 – 2(p) | Hamilton Academical |
| Clyde | 1 – 1(p) | Berwick Rangers |
| Cowdenbeath | 0–2 | Livingston |
| Dumbarton | 0–4 | Alloa Athletic |
| East Fife | 3–2 | Partick Thistle |
| Forfar Athletic | 0–1 | Stirling Albion |
| Queen of the South | 1–4 | Inverness Caledonian Thistle |
| Queen's Park | 1–3 | Ayr United |
| Ross County | 4–1 | Montrose |
| Stenhousemuir | 1–0 | East Stirlingshire |
| Stranraer | (p)1 – 1 | Albion Rovers |
| Home team | Score | Away team |
|---|---|---|
| Berwick Rangers | 1–5 | Falkirk |
| Dundee | 0–1 | Alloa Athletic |
| Dundee United | (p)2 – 2 | Stirling Albion |
| East Fife | 0–1 | Motherwell |
| Hamilton Academical | 1–2 | Hibernian |
| Inverness Caledonian Thistle | 0–3 | Aberdeen |
| Livingston | 1–0 | Dunfermline Athletic |
| Morton | 0–1 | Ross County |
| Raith Rovers | 2–0 | Clydebank |
| St Johnstone | 3–0 | Stranraer |
| St Mirren | 1–3 | Ayr United |
| Stenhousemuir | 0–2 | Airdrieonians |
| Home team | Score | Away team |
|---|---|---|
| Airdrieonians | 1–0 | Celtic |
| Heart of Midlothian | 4–2 | Raith Rovers |
| Hibernian | 1–0 | Aberdeen |
| Ross County | 2–0 | Dundee United |
| Falkirk | 0–1 | St Johnstone |
| Kilmarnock | 3–1 | Livingston |
| Motherwell | 0–2 | Ayr United |
| Rangers | 4–0 | Alloa Athletic |
| Home team | Score | Away team |
|---|---|---|
| Heart of Midlothian | (p)1 – 1 | Ross County |
| Ayr United | 0–2 | Rangers |
| Kilmarnock | 0–1 | Airdrieonians |
| St Johnstone | 4–0 | Hibernian |
| St Johnstone | 3–0 | Heart of Midlothian |
|---|---|---|
Dasovic  41' Preston 45' O'Boyle 87' |
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