Games Played on Tue 17 Aug 1999 |
| <-- 15 08 1999 | 1999-00 | 18 08 1999 --> |
| Games played '*' after date indicates 'nominal date' |
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|---|---|---|---|---|---|---|---|---|
| Date | Comp | Rd | Home | Score | Away | Notes | Venue | Crowd |
| Tue Aug 17 1999 | League Cup | R2 | Aberdeen | 1-0 | Livingston | |||
| Tue Aug 17 1999 | League Cup | R2 | Ayr United | 2-1 | Hamilton Accies | |||
| Tue Aug 17 1999 | League Cup | R2 | Clyde | 2-2 | Hibernian | 4-5 L | ||
| Tue Aug 17 1999 | League Cup | R2 | Dundee | 4-0 | Dumbarton | |||
| Tue Aug 17 1999 | League Cup | R2 | East Fife | 2-2 | Airdrieonians | 5-4 W | ||
| Tue Aug 17 1999 | League Cup | R2 | Inverness Caledonian Thistle | 2-0 | St Mirren | |||
| Tue Aug 17 1999 | League Cup | R2 | Morton | 1-3 | Alloa Athletic | |||
| 