Games Played on Tue 24 Aug 1999 |
| <-- 22 08 1999 | 1999-00 | 25 08 1999 --> |
| Games played '*' after date indicates 'nominal date' |
||||||||
|---|---|---|---|---|---|---|---|---|
| Date | Comp | Rd | Home | Score | Away | Notes | Venue | Crowd |
| Tue Aug 24 1999 | LCHALL | R2 | Airdrieonians | 1-2 | Alloa Athletic | |||
| Tue Aug 24 1999 | LCHALL | R2 | Clydebank | 4-3 | Forfar Athletic | |||
| Tue Aug 24 1999 | LCHALL | R2 | Hamilton Accies | 0-3 | Inverness Caledonian Thistle | |||
| Tue Aug 24 1999 | LCHALL | R2 | Livingston | 2-1 | Berwick Rangers | |||
| Tue Aug 24 1999 | LCHALL | R2 | Queens Park | 3-1 | Albion Rovers | |||
| Tue Aug 24 1999 | LCHALL | R2 | Ross County | 3-0 | Morton | |||
| Tue Aug 24 1999 | LCHALL | R2 | Stirling Albion | 1-1 | Arbroath | |||
| Tue Aug 24 1999 | LCHALL | R2 | Stranraer | 1-2 | Raith Rovers | |||
| Tue Aug 24 1999 | UEFA | Q1 | CSKA (Sofia) | Portadown | n/a | |||
| Tue Aug 24 1999 | UEFA | Q1 | Shamkir | Kryvbas Kryvyi Rih | n/a | |||
| 