All countries
| 16. Round | East Fife | Inverness | details | 06.12.2025 16:00 | |||
| 1/16-finals | Elgin City | East Fife | details | 09.12.2025 20:45 | |||
| 17. Round | Cove Rangers | East Fife | details | 13.12.2025 16:00 | |||
| 18. Round | East Fife | Peterhead | details | 20.12.2025 16:00 | |||
| 19. Round | East Fife | Kelty Hearts | details | 27.12.2025 16:00 | |||
| 20. Round | Hamilton | East Fife | details | 03.01.2026 16:00 | |||
| 21. Round | Stenhousemuir | East Fife | details | 10.01.2026 16:00 | |||
| 22. Round | East Fife | Queen of South | details | 24.01.2026 16:00 | |||
| 23. Round | East Fife | Montrose | details | 31.01.2026 16:00 | |||
| 24. Round | Inverness | East Fife | details | 07.02.2026 16:00 | |||
| 25. Round | East Fife | Cove Rangers | details | 14.02.2026 16:00 | |||
| 26. Round | Peterhead | East Fife | details | 21.02.2026 16:00 | |||
| 27. Round | East Fife | Alloa | details | 28.02.2026 16:00 | |||
| 28. Round | East Fife | Hamilton | details | 07.03.2026 16:00 | |||
| 29. Round | Kelty Hearts | East Fife | details | 14.03.2026 16:00 | |||
| 30. Round | Queen of South | East Fife | details | 21.03.2026 16:00 | |||
| 31. Round | East Fife | Stenhousemuir | details | 28.03.2026 16:00 | |||
| 32. Round | Montrose | East Fife | details | 04.04.2026 16:00 | |||
| 33. Round | East Fife | Peterhead | details | 11.04.2026 16:00 | |||
| 34. Round | Alloa | East Fife | details | 18.04.2026 16:00 | |||
| 35. Round | East Fife | Inverness | details | 25.04.2026 16:00 | |||
| 36. Round | Cove Rangers | East Fife | details | 02.05.2026 16:00 | |||