Games Played on Sun 14 Nov 1999 |
| <-- 12 11 1999 | 1999-00 | 16 11 1999 --> |
| Games played '*' after date indicates 'nominal date' |
||||||||
|---|---|---|---|---|---|---|---|---|
| Date | Comp | Rd | Home | Score | Away | Notes | Venue | Crowd |
| Sun Nov 14 1999 | L1 | Ayr United | 0-1 | Raith Rovers | n/a | |||
| Sun Nov 14 1999 | L1 | Clydebank | 0-3 | Falkirk | n/a | |||
| Sun Nov 14 1999 | L1 | Dunfermline Athletic | 3-0 | Livingston | n/a | |||
| Sun Nov 14 1999 | L2 | Partick Thistle | 2-0 | Stranraer | n/a | |||
| Sun Nov 14 1999 | L3 | Berwick Rangers | 0-1 | Dumbarton | n/a | |||
| Sun Nov 14 1999 | L3 | Brechin City | 2-0 | Cowdenbeath | n/a | |||
| Sun Nov 14 1999 | L3 | East Fife | 1-4 | Albion Rovers | n/a | |||
| Sun Nov 14 1999 | L3 | East Stirlingshire | 2-0 | Montrose | n/a | |||
| Sun Nov 14 1999 | L3 | Forfar Athletic | 2-2 | Queens Park | n/a | |||
| 