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| 29.01.2000 | Heart of Midlothian | - | Stenhousemuir FC | 3:2 | ||
| St. Mirren FC | - | Aberdeen FC | 1:1 | |||
| Albion Rovers | - | Partick Thistle | 1:2 | |||
| Falkirk FC | - | Peterhead FC | 3:1 | |||
| Arbroath FC | - | Motherwell FC | 1:1 | |||
| Queen Of The South | - | Livingston FC | 0:7 | |||
| Clyde FC | - | Raith Rovers | 3:1 | |||
| Stranraer FC | - | Berwick Rangers | 1:2 | |||
| Clydebank FC | - | Stirling Albion FC | 1:0 | |||
| Hibernian FC | - | Dunfermline Athletic | 4:1 | |||
| Dundee FC | - | Ayr United | 0:0 | |||
| 30.01.2000 | St. Johnstone FC | - | Rangers FC | 0:2 | ||
| Greenock Morton FC | - | Brechin City FC | 1:1 | |||
| Dundee United | - | Clydebank FC (old) | 4:1 | |||
| 05.02.2000 | Kilmarnock FC | - | Alloa Athletic | 0:0 | ||
| 08.02.2000 | Celtic FC | - | Inverness CT | 1:3 | ||
| Entscheidungsspiele | ||||||
|---|---|---|---|---|---|---|
| Aberdeen FC | - | St. Mirren FC | 2:0 | |||
| Brechin City FC | - | Greenock Morton FC | 3:4 i.E. | |||
| 09.02.2000 | Alloa Athletic | - | Kilmarnock FC | 1:0 | ||
| 15.02.2000 | Ayr United | - | Dundee FC | 7:6 i.E. | ||
| 19.02.2000 | Motherwell FC | - | Arbroath FC | 2:0 | ||
