Games Played on Wed 18 Aug 1999 |
| <-- 17 08 1999 | 1999-00 | 21 08 1999 --> |
| Games played '*' after date indicates 'nominal date' |
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|---|---|---|---|---|---|---|---|---|
| Date | Comp | Rd | Home | Score | Away | Notes | Venue | Crowd |
| Wed Aug 18 1999 | League Cup | R2 | Dundee United | 3-1 | Ross County | |||
| Wed Aug 18 1999 | League Cup | R2 | Dunfermline Athletic | 4-0 | Queens Park | |||
| Wed Aug 18 1999 | League Cup | R2 | East Stirlingshire | 0-2 | Falkirk | |||
| Wed Aug 18 1999 | League Cup | R2 | Queen of the South | 1-3 | Heart Of Midlothian | |||
| Wed Aug 18 1999 | League Cup | R2 | Raith Rovers | 2-2 | Motherwell | 4-5 L | ||
| 