 |
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| 23.01.1999 | Aberdeen FC | - | Livingston FC | 0:1 | ||
| Ayr United | - | Kilmarnock FC | 3:0 | |||
| Brechin City FC | - | Albion Rovers | 1:1 | |||
| Celtic FC | - | Clydebank FC (old) | 3:1 | |||
| Falkirk FC | - | Huntly FC | 3:0 | |||
| Greenock Morton FC | - | Dundee FC | 2:1 | |||
| Hibernian FC | - | Stirling Albion FC | 1:1 | |||
| Partick Thistle | - | Dunfermline Athletic | 1:2 | |||
| Raith Rovers | - | Clyde FC | 0:4 | |||
| Rangers FC | - | Stenhousemuir FC | 2:0 | |||
| St. Johnstone FC | - | Forfar Athletic | 1:0 | |||
| St. Mirren FC | - | Hamilton Academical | 1:1 | |||
| Stranraer FC | - | East Stirlingshire FC | 1:0 | |||
| 24.01.1999 | Motherwell FC | - | Heart of Midlothian | 3:1 | ||
| 02.02.1999 | Queen's Park FC | - | Dundee United | 0:0 | ||
| 03.02.1999 | Clydebank FC | - | Ross County FC | 1:1 | ||
| Partidos decisivos | ||||||
|---|---|---|---|---|---|---|
| 02.02.1999 | Albion Rovers | - | Brechin City FC | 3:1 | ||
| Hamilton Academical | - | St. Mirren FC | 1:0 | |||
| Stirling Albion FC | - | Hibernian FC | 2:1 | |||
| 09.02.1999 | Dundee United | - | Queen's Park FC | 1:0 | ||
| 15.02.1999 | Ross County FC | - | Clydebank FC | 2:3 | ||
