| 25 (3 to 6) Jamaica 1(1) - 1(1) Trinidad Tobago (75 to 72) 25: 07DEC2008 |
| 25 (-29 to -38) Barbados 1.5(1) - 2(2) Trinidad Tobago (66 to 75) 25: 05DEC2008 |
| 25 (85 to 66) Trinidad Tobago 1(1) - 3(2) Grenada (-113 to -94) 25: 03DEC2008 |
| 38 (70 to 85) Trinidad Tobago 3.5(3) - 0(0) Cuba (-3 to -18) 38: 19NOV2008 |
| 25 (87 to 70) Trinidad Tobago 1(1) - 2(1) Guyana (-38 to 5) 64: 09NOV2008 |
| 25 (79 to 87) Trinidad Tobago 3(3) - 2(1) Saint Kitts Nevis (-60 to -80) 64: 07NOV2008 |
| 25 (88 to 79) Trinidad Tobago 3(3) - 3(2) Antigua Barbuda (-230 to -221) 25: 05NOV2008 |
| 38 (81 to 88) Trinidad Tobago 7.5(2) - 1(1) United States (-176 to -183) 38: 15OCT2008 |
| 50 (31 to 9) Guatemala 0(0) - 0.5(0) Trinidad Tobago (70 to 81) 25: 11OCT2008 |
| 25 (-189 to -194) United States 3(3) - 5.5(0) Trinidad Tobago (65 to 70) 25: 10SEP2008 |
| 25 (54 to 65) Trinidad Tobago 1.5(1) - 1(1) Guatemala (14 to -8) 50: 06SEP2008 |
| 25 (10 to -1) Cuba 1(1) - 3.5(3) Trinidad Tobago (43 to 54) 25: 20AUG2008 |
| 64 (-126 to -144) Bermuda 0.5(0) - 2(2) Trinidad Tobago (36 to 43) 25: 22JUN2008 |
| 25 (56 to 36) Trinidad Tobago 1(1) - 2.5(2) Bermuda (-177 to -126) 64: 15JUN2008 |
| 25 (68 to 56) Trinidad Tobago 1.5(0) - 3(3) England (91 to 124) 70: 01JUN2008 |