 |
 |
|
|
| 08/01/2000 | Albion Rovers | - | Dalbeattie Star | 0:0 | ||
| Arbroath FC | - | Fraserburgh FC | 0:0 | |||
| Brechin City FC | - | Annan Athletic | 2:2 | |||
| Cowdenbeath FC | - | Clyde FC | 2:3 | |||
| Dumbarton FC | - | Stenhousemuir FC | 0:2 | |||
| Montrose FC | - | Queen Of The South | 1:3 | |||
| Partick Thistle | - | East Stirlingshire FC | 2:1 | |||
| Peterhead FC | - | Forfar Athletic | 2:1 | |||
| Queen's Park FC | - | Berwick Rangers | 1:2 | |||
| Stirling Albion FC | - | East Fife FC | 2:1 | |||
| Stranraer FC | - | Clachnacuddin FC | 1:0 | |||
| Whitehill Welfare | - | Alloa Athletic | 2:2 | |||
| decisive matches | ||||||
|---|---|---|---|---|---|---|
| 15/01/2000 | Annan Athletic | - | Brechin City FC | 2:3 aet | ||
| Fraserburgh FC | - | Arbroath FC | 1:3 | |||
| 19/01/2000 | Dalbeattie Star | - | Albion Rovers | 1:5 | ||
| 29/01/2000 | Alloa Athletic | - | Whitehill Welfare | 2:0 | ||
