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Australia | Scottish League Cup 1999/00 |  |
Final
 | 19.03.2000 | Aberdeen | – | Celtic | 0:2 (0:1) | ||
Glasgow | |||||||
Semifinal
| 16.02.2000 | Celtic | – | Kilmarnock | 1:0 (0:0) | ||
Glasgow | |||||||
| 13.02.2000 | Aberdeen | – | Dundee United | 1:0 (0:0) | ||
Dundee | |||||||
Quarterfinal
| 02.12.1999 | Kilmarnock | – | Hearts | 1:0 | ||
| 01.12.1999 | Aberdeen | – | Rangers | 1:0 aet (0:0, 0:0) | ||
Aberdeen | |||||||
| 01.12.1999 | Celtic | – | Dundee | 1:0 | ||
| 01.12.1999 | Dundee United | – | Motherwell | 3:2 | ||
Third Round
| 13.10.1999 | Ayr United | – | Celtic | 0:4 | ||
| 12.10.1999 | Aberdeen | – | Falkirk | 1:1 aet, pen. 5:3 | ||
| 12.10.1999 | Alloa Athletic | – | Dundee | 1:3 | ||
| 12.10.1999 | East Fife | – | Hearts | 0:2 | ||
| 12.10.1999 | Inverness | – | Motherwell | 0:1 | ||
| 12.10.1999 | Kilmarnock | – | Hibernian | 3:2 | ||
| 12.10.1999 | Rangers | – | Dunfermline Athletic | 1:0 | ||
| 12.10.1999 | St. Johnstone | – | Dundee United | 1:2 | ||
Second Round
| 18.08.1999 | Dundee United | – | Ross County | 3:1 aet (1:1) | ||
| 18.08.1999 | Dunfermline Athletic | – | Queen's Park | 4:0 | ||
| 18.08.1999 | East Stirlingshire | – | Falkirk | 0:2 aet (0:0) | ||
| 18.08.1999 | Queen of the South | – | Hearts | 1:3 | ||
| 18.08.1999 | Raith Rovers | – | Motherwell | 2:2 aet, pen. 4:5 | ||
| 17.08.1999 | Aberdeen | – | Livingston | 1:0 | ||
| 17.08.1999 | Ayr United | – | Hamilton Academical | 2:1 | ||
| 17.08.1999 | Clyde | – | Hibernian | 2:2 aet, pen. 4:5 | ||
| 17.08.1999 | Dundee | – | Dumbarton | 4:0 | ||
| 17.08.1999 | East Fife | – | Airdrieonians | 2:2 aet, pen. 5:4 | ||
| 17.08.1999 | Greenock Morton | – | Alloa Athletic | 1:3 | ||
| 17.08.1999 | Inverness | – | St. Mirren | 2:0 aet (0:0) | ||
First Round
| 31.07.1999 | Albion Rovers | – | Clyde | 0:3 aet (0:0) | ||
| 31.07.1999 | Brechin City | – | Dumbarton | 0:2 | ||
| 31.07.1999 | Clydebank | – | East Stirlingshire | 1:2 | ||
| 31.07.1999 | Cowdenbeath | – | Livingston | 1:3 | ||
| 31.07.1999 | East Fife | – | Stirling Albion | 2:2 aet, pen. 8:7 | ||
| 31.07.1999 | Montrose | – | Hamilton Academical | 1:2 | ||
| 31.07.1999 | Partick Thistle | – | Alloa Athletic | 0:2 | ||
| 31.07.1999 | Queen of the South | – | Arbroath | 1:0 aet (0:0) | ||
| 31.07.1999 | Queen's Park | – | Berwick Rangers | 2:1 | ||
| 31.07.1999 | Ross County | – | Forfar Athletic | 2:1 aet (1:1) | ||
| 31.07.1999 | Stenhousemuir | – | Inverness | 1:3 | ||
| 31.07.1999 | Stranraer | – | Raith Rovers | 0:1 aet (0:0) | ||
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