| Pokal 1. Runde am 25.04.2009 |
| Dundee United FC (A) : Unst FC (A) | Greenock Morton FC : Inverness Caledonian FC |
| Ayr United : Ross County FC (LC) | Heart of Midlothian FC : Motherwell FC |
| Hibernian FC : Livingston FC | Clyde FC : Partick Thistle FC |
| St. Johnstone FC (M) : Aberdeen FC (A) | Kilmarnock FC : Dundee FC |