Season Description The CONCACAF qualification process is identical to that for the 2006 FIFA World Cup qualification, except that as Puerto Rico competed this time (they were the only CONCACAF member not to enter 2006 qualification), there were 11 matches instead of 10 in the first preliminary round, and thus 13 teams instead of 14 received a bye to the second preliminary round. The two preliminary rounds, played in the first half of 2008, reduced the 35 entrants to 24 and then 12 teams. Three semi-final groups of four were played between August and November 2008, with the top two in each group advancing to a final six-team group held during 2009. The top three of this group qualified for the World Cup finals; the fourth-placed team advancing to the play-off against the fifth-placed CONMEBOL team.
Round 1 Cuba vs Trinidad and Tobago - 00:00:00 El Salvador vs Trinidad and Tobago - 01:00:00
Round 2 Trinidad and Tobago vs Bermuda - 21:30:00 Bermuda vs Trinidad and Tobago - 22:30:00 Trinidad and Tobago vs Guatemala - 21:30:00 Trinidad and Tobago vs Honduras - 23:00:00
Round 3 USA vs Trinidad and Tobago - 00:10:00 USA vs Trinidad and Tobago - 23:45:00
Round 4 Guatemala vs Trinidad and Tobago - 02:00:00 Trinidad and Tobago vs Costa Rica - 22:05:00
Round 5 Trinidad and Tobago vs USA - 00:10:00 Mexico vs Trinidad and Tobago - 01:30:00
Round 6 Trinidad and Tobago vs Cuba - 01:10:00 Trinidad and Tobago vs El Salvador - 23:30:00
Round 7 Honduras vs Trinidad and Tobago - 01:00:00
Round 8 Trinidad and Tobago vs USA - 23:11:00
Round 9 Costa Rica vs Trinidad and Tobago - 02:00:00
Round 10 Trinidad and Tobago vs Mexico - 00:05:00
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