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| 02.01.1999 | Civil Service Strollers | - | Albion Rovers | 0:3 | ||
| Dalbeattie Star | - | East Stirlingshire FC | 1:2 | |||
| Forfar Athletic | - | East Fife FC | 2:2 | |||
| Huntly FC | - | Peterhead FC | 3:0 | |||
| Inverness CT | - | Livingston FC | 1:2 | |||
| Keith FC | - | Brechin City FC | 0:0 | |||
| Montrose FC | - | Stirling Albion FC | 0:0 | |||
| Partick Thistle | - | Cowdenbeath FC | 5:2 | |||
| The Spartans FC | - | Clyde FC | 1:1 | |||
| Whitehill Welfare | - | Stenhousemuir FC | 1:1 | |||
| 09.01.1999 | Queen Of The South | - | Ross County FC | 1:3 | ||
| 18.01.1999 | Queen's Park FC | - | Clachnacuddin FC | 1:1 | ||
| Entscheidungsspiele | ||||||
|---|---|---|---|---|---|---|
| 06.01.1999 | Clyde FC | - | The Spartans FC | 5:0 | ||
| 09.01.1999 | Brechin City FC | - | Keith FC | 3:1 | ||
| East Fife FC | - | Forfar Athletic | 0:1 | |||
| Stenhousemuir FC | - | Whitehill Welfare | 2:0 | |||
| 18.01.1999 | Stirling Albion FC | - | Montrose FC | 2:1 | ||
| 23.01.1999 | Clachnacuddin FC | - | Queen's Park FC | 2:3 | ||
