| Tuesday 15th August 2000 | |||
| Scottish Challenge Cup First Round | |||
| Airdrieonians | 2-1 | Queen of the South | aet |
| Albion Rovers | 0-1 | Clydebank | |
| Alloa Athletic | 2-3 | Inverness CT | |
| Brechin City | 3-1 | Ayr United | |
| Cowdenbeath | 2-1 | Falkirk | aet |
| East Stirlingshire | 3-0 | East Fife | |
| Elgin City | 2-4 | Dumbarton | |
| Forfar Athletic | 1-1 | Peterhead | aet |
| (Peterhead won on penalties) | |||
| Partick Thistle | 0-2 | Livingston | |
| Queen's Park | 2-0 | Montrose | |
| Raith Rovers | 0-4 | Morton | |
| Ross County | 2-1 | Clyde | |
| Stirling Albion | 2-3 | Arbroath | |
| Stranraer | 4-2 | Berwick Rangers | |
| World Cup South America Qualifying Round Group | |||
| Chile | 3-0 | Brazil | |
| Colombia | 1-0 | Uruguay | |
| World Cup North-Central America Qualifying Semi-Final Round Group 1 | |||
| Mexico | 2-0 | Canada | |
| World Cup North-Central America Qualifying Semi-Final Round Group 3 | |||
| Costa Rica | 2-1 | Guatemala | |
» Results : Tuesday 15th August 2000
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