Games Played on Tue 12 Oct 1999 |
| <-- 09 10 1999 | 1999-00 | 13 10 1999 --> |
| Games played '*' after date indicates 'nominal date' |
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|---|---|---|---|---|---|---|---|---|
| Date | Comp | Rd | Home | Score | Away | Notes | Venue | Crowd |
| Tue Oct 12 1999 | League Cup | R3 | Aberdeen | 1-1 | Falkirk | 5-3 W | ||
| Tue Oct 12 1999 | League Cup | R3 | Alloa Athletic | 1-3 | Dundee | |||
| Tue Oct 12 1999 | League Cup | R3 | East Fife | 0-2 | Heart Of Midlothian | |||
| Tue Oct 12 1999 | League Cup | R3 | Inverness Caledonian Thistle | 0-1 | Motherwell | |||
| Tue Oct 12 1999 | League Cup | R3 | Kilmarnock | 3-2 | Hibernian | |||
| Tue Oct 12 1999 | League Cup | R3 | Rangers | 1-0 | Dunfermline Athletic | |||
| Tue Oct 12 1999 | League Cup | R3 | St Johnstone | 1-2 | Dundee United | |||
| 