You guys may already be aware and I know some people doh like this sort of time wastin on the boards....but
You can manage T&T in the current World Cup qualifying in the game Football Manager 2005 ( apparently in some non-UK markets it is called World Soccer Manager 2005) the simulation starts from the Concacaf semi-final group stages. Though some of the info on the players and the team is dated and to tell you the truth I aint heard of some of the players they say are Trini's,most of the major players are there (some with accurate photo's!). Nakhid was missing and Yorke/Lata's classed as retired from international ball. However the game comes with an editor so these problems are easily solved. The one annoying thing is the groups are randomly generated so it is extremely unlikely that you will be matched against the exact teams we faced. On an interesting note, Yuh man Richard Goddard is in the game with proper posistion! Fuh those who are interested this is made by the people that made the original Championship Manager games, Sports interactive
http://www.sigames.com/ . Forget the new Championship Manager series it is bugged to hell. To manage T&T in the game all you do is generate a new game then set the database to at least large then select the option to generate all players from T&T. When you get to the option to select a team to manage T&T will be in the national teams section.
The game is even more indepth than previous Championship Manager games, seriously addictive if you like simulation gaming.