| Date | Team VS Team | Venue | Winner |
| 04 Sep | 1. Trinbago Knight Riders VS St Kitts & Nevis Patriots | Port of Spain | Trinbago |
| 05 Sep | 2. Guyana Amazon Warriors VS St Lucia Zouks | Guyana | Guyana |
| 06 Sep | 3. Trinbago Knight Riders VS Jamaica Tallawahs | Port of Spain | Trinbago |
| 07 Sep | 4. Guyana Amazon Warriors VS St Kitts & Nevis Patriots | Guyana | Guyana |
| 08 Sep | 5. Trinbago Knight Riders VS St Lucia Zouks | Port of Spain | Trinbago |
| 08 Sep | 6. Guyana Amazon Warriors VS Barbados Tridents | Guyana | Guyana |
| 10 Sep | 7. St Kitts & Nevis Patriots VS Jamaica Tallawahs | St Kitts | St Kitts & Nevis |
| 11 Sep | 8. St Kitts & Nevis Patriots VS Barbados Tridents | St Kitts | Barbados |
| 12 Sep | 9. Jamaica Tallawahs VS St Lucia Zouks | St Kitts | St Lucia |
| 13 Sep | 10. Jamaica Tallawahs VS Trinbago Knight Riders | Jamaica | Trinbago |
| 14 Sep | 11. St Kitts & Nevis Patriots VS GA | Jamaica | Guyana |
| 15 Sep | 12. Jamaica Tallawahs VS Barbados Tridents | St Kitts | Jamaica |
| 15 Sep | 13. St Kitts & Nevis Patriots VS St Lucia Zouks | Jamaica | St Kitts & Nevis |
| 17 Sep | 14. St Kitts & Nevis Patriots VS Trinbago Knight Riders | St Kitts | St Kitts & Nevis |
| 18 Sep | 15. Jamaica Tallawahs VS Guyana Amazon Warriors | St Kitts | Guyana |
| 19 Sep | 16. Jamaica Tallawahs VS St Kitts & Nevis Patriots | Jamaica | St Kitts & Nevis |
| 20 Sep | 17. St Lucia Zouks VS Barbados Tridents | Jamaica | Barbados |
| 21 Sep | 18. St Lucia Zouks VS Trinbago Knight Riders | St Lucia | No Result |
| 22 Sep | 19. Barbados Tridents VS Guyana Amazon Warriors | St Lucia | Guyana |
| 23 Sep | 20. Barbados Tridents VS Jamaica Tallawahs | Barbados | Jamaica |
| 24 Sep | 21. St Lucia Zouks St Kitts & Nevis Patriots | Barbados | St Lucia |
| 25 Sep | 22. St Lucia Zouks VS Guyana Amazon Warriors | St Lucia | Guyana |
| 26 Sep | 23. Barbados Tridents VS Trinbago Knight Riders | St Lucia | Barbados |
| 27 Sep | 24. St Lucia Zouks VS Jamaica Tallawahs | Barbados | St Lucia |
| 28 Sep | 25. Barbados Tridents VS St Kitts & Nevis Patriots | St Lucia | St Kitts & Nevis |
| 29 Sep | 26. Barbados Tridents VS St Lucia Zouks | Barbados | Barbados |
| 30 Sep | 27. Trinbago Knight Riders VS Guyana Amazon Warriors | Barbados | Guyana |
| 02 Oct | 28. Trinbago Knight Riders VS Barbados Tridents | Port of Spain | Barbados |
| 03 Oct | 29. Guyana Amazon Warriors VS Jamaica Tallawahs | Port of Spain | Guyana |
| 04 Oct | 30. Guyana Amazon Warriors VS Trinbago Knight Riders | Guyana | Guyana |
| 06 Oct | E. St Kitts & Nevis Patriots VS Trinbago Knight Riders | Guyana | Trinbago |
| 06 Oct | Q1, Guyana Amazon Warriors VS Barbados Tridents | Guyana | Guyana |
| 10 Oct | Q2, Trinbago Knight Riders VS Barbados Tridents | Guyana | Barbados |
| 12 Oct | F, Guyana Amazon Warriors VS Barbados Tridents | Tarouba | Barbados |