| 1. Round | 30/07/1999 | Hibernian FC | - | Motherwell FC | 2:2 | ||||
| 4. Round | 20/08/1999 | Kilmarnock FC | - | Motherwell FC | 0:1 |  |
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| 5. Round | 27/08/1999 | Motherwell FC | - | Dundee FC | 0:2 | ||||
| 8. Round | 19/10/1999 | Motherwell FC | - | Aberdeen FC | 5:6 |
| 1. Round | 30/07/1999 | Hibernian FC | - | Motherwell FC | 2:2 | ||||
| 4. Round | 20/08/1999 | Kilmarnock FC | - | Motherwell FC | 0:1 | |
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| 5. Round | 27/08/1999 | Motherwell FC | - | Dundee FC | 0:2 | ||||
| 8. Round | 19/10/1999 | Motherwell FC | - | Aberdeen FC | 5:6 |
| Stephen James Craigan | |
| Born: | 29.10.1976 |
| Place of birth: |
Newtonards, 
Northern Ireland |
| Nationality: |
Northern Ireland
|
| Height: | 182 cm |
| Weight: | 79 kg |
| Position(s): | Centre Back |
| Foot: | right |