1. Round | 02/05/2009 | Hamilton Academical | - | Kilmarnock FC | 2:1 | ![]() |
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2. Round | 09/05/2009 | Kilmarnock FC | - | Falkirk FC | 1:1 | ||||
3. Round | 13/05/2009 | Kilmarnock FC | - | St. Mirren FC | 2:1 | ![]() |
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4. Round | 16/05/2009 | Kilmarnock FC | - | Inverness CT | 1:0 | ||||
5. Round | 23/05/2009 | Motherwell FC | - | Kilmarnock FC | 1:2 |