Games Played on Thu 01 May 1969 |
| <-- 30 04 1969 | 1968-69 | 14 05 1969 --> |
| Games played '*' after date indicates 'nominal date' |
||||||||
|---|---|---|---|---|---|---|---|---|
| Date | Comp | Rd | Home | Score | Away | Notes | Venue | Crowd |
| Thu May 1 1969 | L1 | Dunfermline Athletic | 0-3 | Rangers | n/a | |||
| Thu May 1 1969 | L1 | Hibernian | 4-0 | St Johnstone | n/a | 4240 | ||
| Thu May 1 1969 | L2 | Forfar Athletic | 0-1 | Ayr United | n/a | |||
| Thu May 1 1969 | L2 | Hamilton Accies | 2-1 | Brechin City | n/a | |||
| Thu May 1 1969 | L2 | Montrose | 3-0 | Cowdenbeath | n/a | |||
| 