Who would have thought, then, that only a year later the Reggae Boyz would be very much in the running for a place in the region's six-team final qualifying group for the 2010 FIFA World Cup South Africa? Under the leadership of interim coach Theodore Whitmore, the Caribbean islanders have admirably beaten regional giants Mexico and Honduras in the qualifiers, and a win over Canada next Wednesday could take them through to the final phase at the expense of El Tri or Los Catrachos.
Those two surprise victories have earned Jamaica 126 ranking points, making them the highest movers on this month's world ladder with a surge of 33 places from 116th (their lowest all-time position) to 83rd. And while it is true they are still a long way short of their highest ever placing, 27th in August 1998, at least they are now only two spots behind Canada, the team they have to beat in Kingston next week to keep their South Africa 2010 dreams alive.
Two unforgettable games
For incoming coach John Barnes, the first task will be to consolidate the progress made under Whitmore and secure that coveted berth in the North, Central America and Caribbean Zone's hexagonal stage. To this end, the former Liverpool and England player will be carefully analysing Jamaica's two pivotal wins last month in Group 2.
The dream began to take shape against Mexico, a country they had beaten only once before in their history. Amid a wonderful atmosphere at Kingston's National stadium, the home fans saw their heroes take the lead courtesy of a rasping 25-metre strike from Ricardo Fuller that flew into the top corner of Oswaldo Sanchez's goal on 34 minutes. What followed was a master class in tactics and discipline, with Whitmore's charges rendering Mexico's key men redundant to hold out for a historic triumph.
Four days later, when Honduras came to town, the story was remarkably similar. On this occasion, a Luton Shelton strike on 16 minutes put the Reggae Boyz ahead, and once again a c****ination of formidable local support and intelligent play brought them victory by the narrowest of margins.
The stage is thus set for a dramatic conclusion to Group 2 next week. After failing to win any of their first three games, Jamaica are now third in the section with seven points, two behind Honduras and three behind Mexico, the two teams who face off in the group's other remaining game.
With an inferior goal difference to the top two, the Caribbean islanders know that only a win will give them a chance of progressing. Yet Jamaica have beaten the odds before in this campaign, so who is to say they cannot do it again next Wednesday and continue to make history in Kingston.