| 2. Jornada | 11.08.2018 | Raith Rovers | - | Stenhousemuir FC | 2:0 |  |
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| 3. Jornada | 18.08.2018 | Raith Rovers | - | East Fife FC | 2:2 | |
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| 6. Jornada | 15.09.2018 | Brechin City FC | - | Raith Rovers | 1:1 | |
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| 26. Jornada | 23.02.2019 | Raith Rovers | - | Montrose FC | 4:1 | |
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| 27. Jornada | 02.03.2019 | Stranraer FC | - | Raith Rovers | 2:2 | |
Escocia