All countries
| 23. Round | Waterhouse | Tivoli | 1:1 (1:1, 0:0) | details | 16.02.2026 | |||
| 22. Round | Tivoli | Arnett Gardens | 0:2 (0:1, 0:1) | details | 08.02.2026 | |||
| 21. Round | Harbour View | Tivoli | 2:2 (1:2, 1:0) | details | 01.02.2026 | |||
| 12. Round | Tivoli | Treasure Beach | 0:0 (0:0, 0:0) | details | 28.01.2026 | |||
| 20. Round | Cavalier | Tivoli | 1:2 (0:0, 1:2) | details | 25.01.2026 | |||
| 19. Round | Tivoli | Racing United | 0:0 (0:0, 0:0) | details | 22.01.2026 | |||
| 18. Round | Molynes | Tivoli | 3:2 (1:1, 2:1) | details | 19.01.2026 | |||
| 17. Round | Tivoli | Montego Bay | 0:1 (0:0, 0:1) | details | 15.01.2026 | |||
| 16. Round | Spanish Town Police | Tivoli | 0:1 (0:0, 0:1) | details | 12.01.2026 | |||
| 15. Round | Tivoli | Portmore | 2:2 (1:1, 1:1) | details | 05.01.2026 | |||
| 14. Round | Tivoli | Chapelton | 2:0 (1:0, 1:0) | details | 29.12.2025 | |||
| 13. Round | Dunbeholden | Tivoli | 1:0 (0:0, 1:0) | details | 21.12.2025 | |||
| 11. Round | Mount Pleasant | Tivoli | 5:0 (2:0, 3:0) | details | 11.12.2025 | |||
| 10. Round | Tivoli | Waterhouse | 2:1 (1:0, 1:1) | details | 09.12.2025 | |||
| 9. Round | Arnett Gardens | Tivoli | 1:2 (0:1, 1:1) | details | 21.10.2025 | |||
| 8. Round | Tivoli | Harbour View | 2:1 (1:1, 1:0) | details | 12.10.2025 | |||
| 7. Round | Tivoli | Cavalier | 0:2 (0:0, 0:2) | details | 05.10.2025 | |||
| 6. Round | Racing United | Tivoli | 0:0 (0:0, 0:0) | details | 28.09.2025 | |||
| 5. Round | Tivoli | Molynes | 1:1 (0:0, 1:1) | details | 21.09.2025 | |||
| 4. Round | Montego Bay | Tivoli | 3:1 (3:0, 0:1) | details | 15.09.2025 | |||
| 3. Round | Tivoli | Spanish Town Police | 2:1 (2:0, 0:1) | details | 09.09.2025 | |||
| 2. Round | Portmore | Tivoli | 0:0 (0:0, 0:0) | details | 01.09.2025 | |||
| 1. Round | Chapelton | Tivoli | 2:1 (1:1, 1:0) | details | 24.08.2025 | |||
| Quarter-finals - Second leg | Montego Bay | Tivoli | 1:1 (0:0, 1:1) | details | 13.05.2025 | |||
| Quarter-finals - First leg | Tivoli | Montego Bay | 1:2 (0:0, 1:2) | details | 10.05.2025 | |||
| 39. Round | Tivoli | Montego Bay | 2:1 (2:1, 0:0) | details | 04.05.2025 | |||
| 38. Round | Chapelton | Tivoli | 2:2 (0:1, 2:1) | details | 27.04.2025 | |||
| 37. Round | Tivoli | Harbour View | 2:1 (1:1, 1:0) | details | 20.04.2025 | |||
| 36. Round | Vere United | Tivoli | 1:2 (1:1, 0:1) | details | 13.04.2025 | |||
| 35. Round | Arnett Gardens | Tivoli | 0:0 (0:0, 0:0) | details | 08.04.2025 | |||
| 34. Round | Tivoli | Cavalier | 1:1 (1:0, 0:1) | details | 03.04.2025 | |||
| 33. Round | Mount Pleasant | Tivoli | 0:0 (0:0, 0:0) | details | 30.03.2025 | |||
| 32. Round | Tivoli | Racing United | 1:0 (0:0, 1:0) | details | 23.03.2025 | |||
| 31. Round | Dunbeholden | Tivoli | 2:4 (1:1, 1:3) | details | 19.03.2025 | |||
| 30. Round | Tivoli | Waterhouse | 3:2 (1:1, 2:1) | details | 16.03.2025 | |||
| 27. Round | Tivoli | Molynes | 3:0 (2:0, 1:0) | details | 12.03.2025 | |||
| 29. Round | Portmore | Tivoli | 1:1 (0:0, 1:1) | details | 09.03.2025 | |||
| 28. Round | Humble Lions | Tivoli | 3:2 (1:0, 2:2) | details | 06.03.2025 | |||
| 24. Round | Harbour View | Tivoli | 2:2 (0:2, 2:0) | details | 23.02.2025 | |||
| 23. Round | Tivoli | Vere United | 2:1 (2:1, 0:0) | details | 20.02.2025 | |||
| 26. Round | Montego Bay | Tivoli | 3:1 (1:0, 2:1) | details | 18.02.2025 | |||
| 25. Round | Tivoli | Chapelton | 1:1 (1:1, 0:0) | details | 12.02.2025 | |||
| 22. Round | Tivoli | Arnett Gardens | 3:5 (2:1, 1:4) | details | 04.02.2025 | |||
| 21. Round | Cavalier | Tivoli | 0:0 (0:0, 0:0) | details | 30.01.2025 | |||
| 20. Round | Tivoli | Mount Pleasant | 0:1 (0:1, 0:0) | details | 26.01.2025 | |||
| 19. Round | Racing United | Tivoli | 2:0 (2:0, 0:0) | details | 23.01.2025 | |||
| 18. Round | Tivoli | Dunbeholden | 2:0 (0:0, 2:0) | details | 19.01.2025 | |||
| 17. Round | Waterhouse | Tivoli | 0:1 (0:0, 0:1) | details | 12.01.2025 | |||
| 16. Round | Tivoli | Portmore | 1:1 (0:1, 1:0) | details | 06.01.2025 | |||
| 15. Round | Tivoli | Humble Lions | 5:1 (3:0, 2:1) | details | 29.12.2024 | |||