SOON TO BE RELEGATED TO THE FOURTH DIVISION OF THE INTERNET
CONCACAF FIRST ROUND GROUP 1C
| SUN 03 FEB 2008 | Hamilton | 19:00 UTC | Bermuda | 01–01 | Cayman Is |
| MON 31 MAR 2008 | Georgetown | 00:00 UTC | Cayman Is | 01–03 | Bermuda |
| SUN 15 JUN 2008 | Macoya | 21:30 UTC | Trinidad-Tobago | 01–02 | Bermuda |
| SUN 22 JUN 2008 | Hamilton | 22:30 UTC | Bermuda | 00–02 | Trinidad-Tobago |
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