| Date | Time | Fixture | Venue |
| 29 June 2016 | 21:00 | Trinbago Knight Riders vs St. Lucia Zouks | Port of Spain |
| 30 June 2016 | 20:00 | St. Kitts Nevis Patriots vs Guyana Amazon Warriors | Basseterre, St Kitts |
| 1 July 2016 | 21:00 | Trinbago Knight Riders vs Barbados Tridents | Port of Spain |
| 2 July 2016 | 12:00 | St. Kitts Nevis Patriots vs Jamaica Tallawahs | Basseterre, St Kitts |
| 2 July 2016 | 21:00 | Trinbago Knight Riders vs Guyana Amazon Warriors | Port of Spain |
| 3 July 2016 | 16:00 | St. Kitts Nevis Patriots vs St. Lucia Zouks | Basseterre, St Kitts |
| 4 July 2016 | 19:00 | Trinbago Knight Riders vs Jamaica Tallawahs | Port of Spain |
| 5 July 2016 | 19:00 | St. Kitts Nevis Patriots vs Barbados Tridents | Basseterre, St Kitts |
| 7 July 2016 | 19:00 | Guyana Amazon Warriors vs Jamaica Tallawahs | Providence, Guyana |
| 9 July 2016 | 12:00 | Guyana Amazon Warriors vs St. Kitts Nevis Patriots | Providence, Guyana |
| 10 July 2016 | 19:00 | Guyana Amazon Warriors vs Trinbago Knight Riders | Providence, Guyana |
| 11 July 2016 | 20:00 | Barbados Tridents vs Jamaica Tallawahs | Barbados |
| 12 July 2016 | 19:00 | Guyana Amazon Warriors vs St. Lucia Zouks | Providence, Guyana |
| 13 July 2016 | 20:00 | Barbados Tridents vs St. Kitts Nevis Patriots | Barbados |
| 15 July 2016 | 20:00 | Jamaica Tallawahs vs Guyana Amazon Warriors | Jamaica |
| 16 July 2016 | 12:00 | Barbados Tridents vs Trinbago Knight Riders | Barbados |
| 16 July 2016 | 18:00 | Jamaica Tallawahs vs St. Kitts Nevis Patriots | Jamaica |
| 17 July 2016 | 19:00 | Barbados Tridents vs St. Lucia Zouks | Barbados |
| 18 July 2016 | 20:00 | Jamaica Tallawahs vs Trinbago Knight Riders | Jamaica |
| 20 July 2016 | 20:00 | Jamaica Tallawahs vs Barbados Tridents | Jamaica |
| 21 July 2016 | 18:00 | St. Lucia Zouks vs St. Kitts Nevis Patriots | St Lucia |
| 23 July 2016 | 12:00 | St. Lucia Zouks vs Barbados Tridents | St Lucia |
| 24 July 2016 | 17:00 | St. Lucia Zouks vs Guyana Amazon Warriors | St Lucia |
| 26 July 2016 | 18:00 | St. Lucia Zouks vs Trinbago Knight Riders | St Lucia |
| 28 July 2016 | 19:00 | Guyana Amazon Warriors vs Barbados Tridents | Florida |
| 29 July 2016 | 19:00 | St. Kitts Nevis Patriots vs Trinbago Knight Riders | Florida |
| 30 July 2016 | 12:00 | St. Lucia Zouks vs Jamaica Tallawahs | Florida |
| 30 July 2016 | 16:00 | Barbados Tridents vs Guyana Amazon Warriors | Florida |
| 31 July 2016 | 12:00 | Trinbago Knight Riders vs St. Kitts Nevis Patriots | Florida |
| 31 July 2016 | 16:00 | Jamaica Tallawahs vs St. Lucia Zouks | Florida |
| 3 August 2016 | 19:00 | Playoff-1 | St. Kitts |
| 4 August 2016 | 19:00 | Playoff-2 | St. Kitts |
| 5 August 2016 | 20:00 | Playoff-3 | St. Kitts |
| 7 August 2016 | 19:00 | Final | St. Kitts |
