| 25 Jan 2008 | Preliminary Round | Cuba v St Maarten | Coolidge Cricket Ground, Coolidge | Results |
| 26 Jan 2008 | Preliminary Round | Cayman Islands v St Lucia | Coolidge Cricket Ground, Coolidge | Results |
| 27 Jan 2008 | Preliminary Round | British Virgin Islands v Dominica | Coolidge Cricket Ground, Coolidge | Results |
| 29 Jan 2008 | Preliminary Round | Montserrat v Turks and Caicos Islands | Coolidge Cricket Ground, Coolidge | Results |
| 30 Jan 2008 | Preliminary Round | St Kitts v United States Virgin Islands | Coolidge Cricket Ground, Coolidge | Results |
| 01 Feb 2008 | First Round | St Maarten v St Vincent and the Grenadines | Coolidge Cricket Ground, Coolidge | Results |
| 02 Feb 2008 | First Round | St Lucia v Trinidad and Tobago | Coolidge Cricket Ground, Coolidge | Results |
| 03 Feb 2008 | First Round | Anguilla v Grenada | Coolidge Cricket Ground, Coolidge | Results |
| 05 Feb 2008 | First Round | Barbados v Dominica | Coolidge Cricket Ground, Coolidge | Results |
| 06 Feb 2008 | First Round | Bahamas v Jamaica | Coolidge Cricket Ground, Coolidge | Results |
| 08 Feb 2008 | First Round | Montserrat v Nevis | Coolidge Cricket Ground, Coolidge | Results |
| 09 Feb 2008 | First Round | Antigua and Barbuda v United States Virgin Islands | Coolidge Cricket Ground, Coolidge | Results |
| 10 Feb 2008 | First Round | Bermuda v Guyana | Coolidge Cricket Ground, Coolidge | Results |
| 13 Feb 2008 | Quarter-Final | St Vincent and the Grenadines v Trinidad and Tobago | Coolidge Cricket Ground, Coolidge | Results |
| 15 Feb 2008 | Quarter-Final | Barbados v Grenada | Coolidge Cricket Ground, Coolidge | Results |
| 16 Feb 2008 | Quarter-Final | Jamaica v Nevis | Coolidge Cricket Ground, Coolidge | Results |
| 17 Feb 2008 | Quarter-Final | Antigua and Barbuda v Guyana | Coolidge Cricket Ground, Coolidge | Results |
| 22 Feb 2008 | Semi Final | Barbados v Trinidad and Tobago | Coolidge Cricket Ground, Coolidge | Results |
| 23 Feb 2008 | Semi Final | Guyana v Jamaica | Coolidge Cricket Ground, Coolidge | Results |
| 24 Feb 2008 | Final | Jamaica v Trinidad and Tobago | Coolidge Cricket Ground, Coolidge | Results |
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