| Friday, January 25th 2008 |
| Match 1 |
Cuba vs St Maarten - Cancelled (St Maarten receive a bye)
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| Saturday, January 26th 2008 |
| Match 2 |
St. Lucia beat Cayman Islands by 46 runs
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| Sunday, Janury 27th 2008 |
| Match 3 |
Dominica beat British Virgin Islands by 66 runs |
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| Tuesday, January 29th 2008 |
| Match 4 |
Montserrat beat Turks & Caicos by 9 wickets |
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| Wednesday, January 30th 2008 |
| Match 5 |
US Virgin Islands beat St. Kitts by 4 wickets |
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| Friday, February 1st 2008 |
| Match 6 |
St. Vincent and the Grenadins beat St Maarten by 10 runs
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| Saturday, February 2nd 2008 |
| Match 7 |
Trinidad and Tobago beat St. Lucia by 8 wickets
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| Sunday, February 3rd 2008 |
| Match 8 |
Grenada beat Anguilla by 16 runs
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| Tuesday, February 5th 2008 |
| Match 9 |
Barbados beat Dominica by 26 runs
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| Wednesday, February 6th 2008 |
| Match 10 |
Jamaica beat Bahamas by 118 runs
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| Friday, February 8th 2008 |
| Match 11 |
Nevis beat Montserrat by 74 runs
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| Saturday, February 9th 2008 |
| Match 12 |
Antigua and Barbuda beat US Virgin Islands by 24 runs
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| Sunday, February 10th 2008 |
| Match 13 |
Guyana beat Bermuda by 9 wickets
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| Wednesday, February 13th 2008 - Quater Final |
| Match 14 |
Trinidad and Tobago beat St. Vincent and the Grenadins by
59 runs
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| Friday, February 15th 2008 - Quater Final |
| Match 15 |
Barbados beat Grenada by 54 runs
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| Saturday, February 16th 2008 - Quater Final |
| Match 16 |
Jamaica beat Nevis by 8 wickets
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| Sunday, February 17th 2008 - Quater Final |
| Match 17 |
Guyana beat Antigua and Barbuda by 10 runs
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| Friday, February 22nd 2008 - Semi Final 1 |
| Match 18 |
Trinidad and Tobago beat Barbados by 5 runs |
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| Saturday, February 23rd 2008 - Semi Final 2 |
| Match 19 |
Jamaica beat Guyana by 1 run
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| Sunday, February 24th 2008 - Final |
| Match 20 |
Trinidad and Tobago beat Jamaica by 9 wickets
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