| 1 | Tue 14 Jul | 210-0 v KilmarnockKilmarnock 0-0 Raith Rovers | Viaplay Cup Group H |
| 2 | Sat 18 Jul | 211-1 v Hamilton AcademicalHamilton Academical 1-1 Raith Rovers | Viaplay Cup Group H |
| 3 | Sat 1 Aug | 211-1 v StenhousemuirRaith Rovers 1-1 Stenhousemuir | William Hill Championship |
| 4 | Sat 8 Aug | 21 2-1 v Queens ParkQueens Park 1-2 Raith Rovers | William Hill Championship |
| 5 | Sat 22 Aug | 21 2-0 v Ayr UnitedRaith Rovers 2-0 Ayr United | William Hill Championship |
| 6 | Fri 28 Aug | 210-1 v Dunfermline AthleticDunfermline Athletic 1-0 Raith Rovers | William Hill Championship |
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