| 11 Jul 2006 | Preliminary Round | St Maarten v United States Virgin Islands | Coolidge Cricket Ground, Coolidge | Results |
| 11 Jul 2006 | Preliminary Round | Bahamas v Cayman Islands | Coolidge Cricket Ground, Coolidge | Results |
| 12 Jul 2006 | Preliminary Round | British Virgin Islands v St Lucia | Coolidge Cricket Ground, Coolidge | Results |
| 14 Jul 2006 | First Round | Dominica v Grenada | Coolidge Cricket Ground, Coolidge | Results |
| 14 Jul 2006 | First Round | Nevis v St Kitts | Coolidge Cricket Ground, Coolidge | Results |
| 18 Jul 2006 | First Round | St Vincent and the Grenadines v United States Virgin Islands | Coolidge Cricket Ground, Coolidge | Results |
| 18 Jul 2006 | First Round | Anguilla v Barbados | Coolidge Cricket Ground, Coolidge | Results |
| 19 Jul 2006 | First Round | Antigua and Barbuda v St Lucia | Coolidge Cricket Ground, Coolidge | Results |
| 21 Jul 2006 | First Round | Guyana v Montserrat | Coolidge Cricket Ground, Coolidge | Results |
| 21 Jul 2006 | First Round | Bermuda v Jamaica | Coolidge Cricket Ground, Coolidge | Results |
| 25 Jul 2006 | First Round | Cayman Islands v Trinidad and Tobago | Coolidge Cricket Ground, Coolidge | Results |
| 26 Jul 2006 | Quarter-Final | Grenada v St Vincent and the Grenadines | Coolidge Cricket Ground, Coolidge | Results |
| 26 Jul 2006 | Quarter-Final | Antigua and Barbuda v Nevis | Coolidge Cricket Ground, Coolidge | Results |
| 28 Jul 2006 | Quarter-Final | Barbados v Trinidad and Tobago | Coolidge Cricket Ground, Coolidge | Results |
| 28 Jul 2006 | Quarter-Final | Guyana v Jamaica | Coolidge Cricket Ground, Coolidge | Results |
| 10 Aug 2006 | Semi-Final | Grenada v Guyana | Coolidge Cricket Ground, Coolidge | Results |
| 11 Aug 2006 | Semi-Final | Nevis v Trinidad and Tobago | Coolidge Cricket Ground, Coolidge | Results |
| 13 Aug 2006 | Final | Guyana v Trinidad and Tobago | Coolidge Cricket Ground, Coolidge | Results |
| 29 Jul 2006 | Quarter-Final Replay | Barbados v Trinidad and Tobago | Coolidge Cricket Ground, Coolidge | Results |
| 29 Jul 2006 | Quarter-Final Replay | Guyana v Jamaica | Coolidge Cricket Ground, Coolidge | Results |
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