| 1st Match | T20 | Jamaica Kingsmen v Antigua and Barbuda Falcons | Arnos Vale Ground, Kingstown, St Vincent | Antigua and Barbuda Falcons won by 2 wkts |
| 2nd Match | T20 | St Kitts and Nevis Patriots v Trinbago Knight Riders | Arnos Vale Ground, Kingstown, St Vincent | Trinbago Knight Riders won by 19 runs (DLS Method) |
| 3rd Match | T20 | Saint Lucia Kings v Antigua and Barbuda Falcons | Arnos Vale Ground, Kingstown, St Vincent | Saint Lucia Kings won by 4 runs |
| 4th Match | T20 | Barbados Tridents v Jamaica Kingsmen | Sabina Park, Kingston, Jamaica | Barbados Tridents won by 5 runs |
| 5th Match | T20 | Saint Lucia Kings v St Kitts and Nevis Patriots | Daren Sammy National Cricket Stadium, Gros Islet, St Lucia | St Kitts and Nevis Patriots won by 5 wkts |
| 6th Match | T20 | Jamaica Kingsmen v Guyana Amazon Warriors | Sabina Park, Kingston, Jamaica | Guyana Amazon Warriors won by 6 wkts |
| 7th Match | T20 | Antigua and Barbuda Falcons v Saint Lucia Kings | Daren Sammy National Cricket Stadium, Gros Islet, St Lucia | Saint Lucia Kings won by 3 wkts (2nd innings reduced to 8 overs due to rain, DLS target 52) |
| 8th Match | T20 | Trinbago Knight Riders v Jamaica Kingsmen | Sabina Park, Kingston, Jamaica | Jamaica Kingsmen won by 5 wkts |
| 9th Match | T20 | Barbados Tridents v Saint Lucia Kings | Daren Sammy National Cricket Stadium, Gros Islet, St Lucia | Barbados Tridents won by 9 runs - 18 overs game due to rain |
| 10th Match | T20 | Jamaica Kingsmen v St Kitts and Nevis Patriots | Sabina Park, Kingston, Jamaica | Jamaica Kingsmen won by 51 runs |
| 11th Match | T20 | Saint Lucia Kings v Guyana Amazon Warriors | Daren Sammy National Cricket Stadium, Gros Islet, St Lucia | Guyana Amazon Warriors won by 7 wkts |
| 12th Match | T20 | St Kitts and Nevis Patriots v Antigua and Barbuda Falcons | Sir Vivian Richards Stadium, North Sound, Antigua | Antigua and Barbuda Falcons won by 3 wkts |
| 13th Match | T20 | Jamaica Kingsmen v Saint Lucia Kings | Daren Sammy National Cricket Stadium, Gros Islet, St Lucia | Saint Lucia Kings won by 6 wkts |
| 14th Match | T20 | Trinbago Knight Riders v Antigua and Barbuda Falcons | Sir Vivian Richards Stadium, North Sound, Antigua | Antigua and Barbuda Falcons won by 5 wkts |
| 15th Match | T20 | Antigua and Barbuda Falcons v Guyana Amazon Warriors | Sir Vivian Richards Stadium, North Sound, Antigua | Guyana Amazon Warriors won by 7 wkts |
| 16th Match | T20 | Antigua and Barbuda Falcons v Barbados Tridents | Sir Vivian Richards Stadium, North Sound, Antigua | Antigua and Barbuda Falcons won by 30 runs |
| 17th Match | T20 | Saint Lucia Kings v Trinbago Knight Riders | Queen's Park Oval, Port of Spain, Trinidad | Saint Lucia Kings won by 36 runs |
| 18th Match | T20 | Jamaica Kingsmen v St Kitts and Nevis Patriots | Warner Park, Basseterre, St Kitts | Jamaica Kingsmen won by 11 runs |
| 19th Match | T20 | Barbados Tridents v Trinbago Knight Riders | Queen's Park Oval, Port of Spain, Trinidad | Trinbago Knight Riders won by 7 wkts |
| 20th Match | T20 | Trinbago Knight Riders v Jamaica Kingsmen | Queen's Park Oval, Port of Spain, Trinidad | Jamaica Kingsmen won by 7 runs (DLS Method) |
| 21st Match | T20 | St Kitts and Nevis Patriots v Antigua and Barbuda Falcons | Warner Park, Basseterre, St Kitts | Match abandoned due to rain (with toss) |
| 22nd Match | T20 | Guyana Amazon Warriors v Trinbago Knight Riders | Queen's Park Oval, Port of Spain, Trinidad | Guyana Amazon Warriors won by 9 runs (DLS Method), TKR target 182 |
| 23rd Match | T20 | Barbados Tridents v St Kitts and Nevis Patriots | Warner Park, Basseterre, St Kitts | St Kitts and Nevis Patriots won by 6 wkts |
| 24th Match | T20 | Antigua and Barbuda Falcons v Trinbago Knight Riders | Queen's Park Oval, Port of Spain, Trinidad | Antigua and Barbuda Falcons won by 8 runs |
| 25th Match | T20 | St Kitts and Nevis Patriots v Saint Lucia Kings | Warner Park, Basseterre, St Kitts | St Kitts and Nevis Patriots won by 137 runs |
| 26th Match | T20 | Jamaica Kingsmen v Guyana Amazon Warriors | Providence Stadium, Guyana | Guyana Amazon Warriors won by 8 wkts |
| 27th Match | T20 | Trinbago Knight Riders v Barbados Tridents | Kensington Oval, Bridgetown, Barbados | Trinbago Knight Riders won by 35 runs |
| 28th Match | T20 | St Kitts and Nevis Patriots v Guyana Amazon Warriors | Providence Stadium, Guyana | Guyana Amazon Warriors won by 7 wkts |
| 29th Match | T20 | Saint Lucia Kings v Barbados Tridents | Kensington Oval, Bridgetown, Barbados | Barbados Tridents won by 8 wkts |
| 30th Match | T20 | Antigua and Barbuda Falcons v Guyana Amazon Warriors | Providence Stadium, Guyana | Antigua and Barbuda Falcons won by 65 runs |
| 31st Match | T20 | Saint Lucia Kings v Guyana Amazon Warriors | Providence Stadium, Guyana | Guyana Amazon Warriors won by 4 wkts |
| 32nd Match | T20 | St Kitts and Nevis Patriots v Barbados Tridents | Kensington Oval, Bridgetown, Barbados | Barbados Tridents won by 4 wkts |
| 33rd Match | T20 | Trinbago Knight Riders v Guyana Amazon Warriors | Providence Stadium, Guyana | Guyana Amazon Warriors won by 6 wkts |
| 34th Match | T20 | Jamaica Kingsmen v Barbados Tridents | Kensington Oval, Bridgetown, Barbados | Barbados Tridents won by 2 wkts |
| 35th Match | T20 | Guyana Amazon Warriors v Barbados Tridents | Kensington Oval, Bridgetown, Barbados | Barbados Tridents won by 6 wkts |
| Eliminator | T20 | Barbados Tridents v Jamaica Kingsmen | Kensington Oval, Bridgetown, Barbados | Jamaica Kingsmen won by 9 wkts |
| Qualifier 1 | T20 | Guyana Amazon Warriors v Antigua and Barbuda Falcons | Kensington Oval, Bridgetown, Barbados | Antigua and Barbuda Falcons won by 9 wkts |
| Qualifier 2 | T20 | Guyana Amazon Warriors v Jamaica Kingsmen | Kensington Oval, Bridgetown, Barbados | Jamaica Kingsmen won by 5 wkts |
| Final | T20 | Antigua and Barbuda Falcons v Jamaica Kingsmen | Kensington Oval, Bridgetown, Barbados | Scorecard |