Scottish League Cup 1998/99
| Scottish League Cup | |
| Association | Scottish FA |
| First edition | 1946/47 |
| Game mode | Knockout system |
| Title holder | Glasgow Rangers (21st title) |
| Record winner | Glasgow Rangers (21 wins) |
| Website | scottishfootballleague.com |
The Scottish League Cup was played for the 53rd time in 1998/99 . The Scottish League Cup began on August 1, 1998 and ended with the final in November of that year. The clubs of the Scottish Football League and Scottish Premier League participated in the competition. If a duel was not decided after 90 minutes plus extra time, there was a penalty shoot-out. The Glasgow Rangers secured the title in the final against FC St. Johnstone .
1 round
The matches took place on August 1, 1998.
| Result | ||
|---|---|---|
| FC Arbroath | 0: 1 | Clydebank FC |
| Brechin City | 2: 2 (?:? I. E.) |
Hamilton Academical |
| Clyde FC | 1: 1 (?:? I. E.) |
Berwick Rangers |
| Cowdenbeath FC | 0: 2 | Livingston FC |
| Dumbarton FC | 0: 4 | Alloa Athletic |
| East Fife FC | 3: 2 a.d. | Partick Thistle |
| Forfar Athletic | 0: 1 | Stirling Albion |
| Queen of the South | 1: 4 | Inverness CT |
| FC Queen's Park | 1: 3 | Ayr United |
| Ross County | 4: 1 | Montrose FC |
| FC Stenhousemuir | 1-0 | East Stirlingshire FC |
| FC Stranraer | 1: 1 (?:? I. E.) |
Albion Rovers |
2nd round
The matches took place on August 8, 1998.
| Result | ||
|---|---|---|
| Berwick Rangers | 1: 5 | FC Falkirk |
| Dundee FC | 0: 1 | Alloa Athletic |
| Dundee United | 2: 2 (?:? I. E.) |
Stirling Albion |
| East Fife FC | 0: 1 a.d. | Motherwell FC |
| Hamilton Academical | 1: 2 | Hibernian Edinburgh |
| Inverness CT | 0: 3 | Aberdeen FC |
| Livingston FC | 1: 0 a.d. | Dunfermline Athletic |
| Greenock Morton | 0: 1 | Ross County |
| Raith Rovers | 2-0 | Clydebank FC |
| St. Johnstone FC | 3-0 | FC Stranraer |
| FC St. Mirren | 1: 3 | Ayr United |
| FC Stenhousemuir | 0: 2 | Airdrieonians FC |
3rd round
The matches took place on August 18 and 19, 1998.
| Result | ||
|---|---|---|
| FC Falkirk | 0: 1 | St. Johnstone FC |
| FC Kilmarnock | 3: 1 a.d. | Livingston FC |
| Motherwell FC | 0: 2 | Ayr United |
| Glasgow Rangers | 4-0 | Alloa Athletic |
| Airdrieonians FC | 1-0 | Celtic Glasgow |
| Heart of Midlothian | 4: 2 a.d. | Raith Rovers |
| Hibernian Edinburgh | 1-0 | Aberdeen FC |
| Ross County | 2: 0 a.d. | Dundee United |
Quarter finals
The matches were held on 8./9. September 1998.
| Result | ||
|---|---|---|
| Ayr United | 0: 2 | Glasgow Rangers |
| FC Kilmarnock | 0: 1 a.d. | Airdrieonians FC |
| St. Johnstone FC | 4-0 | Hibernian Edinburgh |
| Heart of Midlothian | 1: 1 (?:? I. E.) |
Ross County |
Semifinals
The matches were held on 25/27. October 1998.
| Result | ||
|---|---|---|
| Glasgow Rangers | 5-0 | Airdrieonians FC |
| St. Johnstone FC | 3-0 | Heart of Midlothian |
final
| Glasgow Rangers | St. Johnstone FC | ||||||
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Antti Niemi - Sergio Porrini , Lorenzo Amoruso , Colin Hendry , Arthur Numan - Giovanni van Bronckhorst , Jörg Albertz (65th Ian Ferguson ), Barry Ferguson , Andrei Kantschelskis - Rod Wallace , Stéphane Guivarc'h (89th Gordon Durie ) Trainer: Dick Advocaat ( Netherlands )  |
Alan Main - John McQuillan , Alan Kernaghan , Darren Dods , Gary Bollan - John O'Neil , Philip Scott , Nick Dasovic , Paul Kane - Miguel Simão (84th Roddy Grant ), George O'Boyle (74th Nathan Lowndes ) Trainers: Sandy Clark |
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 1: 0 Guivarc'h (6th) 2: 1 Albertz (37th)
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1: 1 Dasovic (8.)
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 Dasovic
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