40-year-old Russell Latapy and 36-year-old Dwight Yorke -- who connected for the Caribbean side as Yorke converted a penalty kick in the 79th minute to snap a 1-1 deadlock.
Trinidad needed the three points much more than the USA, who clinched a berth in next year's final CONCACAF round after only four games of the six-match series. Combined with Cuba's 2-1 upset of favored Guatemala in Havana Wednesday night, the Soca Warriors (2-1-2, eight) find themselves in second place behind the U.S. (4-1-0, 12 points). Guatemala (1-2-2, five) is third and Cuba (1-4-0, three) is fourth and last. The top two teams move on to the hexagonal.
"That's a massive result for us," Yorke said told ESPN immediately afterward.
Indeed it was. But so was the victory against the U.S.
"It's enormous for us," Yorke said. "Everyone knows how important it was for us. We left it a little late. ... It's very important for this national to progress into the big six."
T&T will play host Cuba in its final semifinal match on Nov. 19, while the U.S. tussles with Guatemala in Commerce City, Colo. on the same Wednesday.
The U.S., under coach Bob Bradley, deployed a starting lineup that averaged 23.7 years of age -- the youngest being Jozy Altidore 18, the oldest being Frankie Hejduk at 34.
Needing at least a point, T&T used what is considered an ancient lineup for qualifiers as its starting 11 averaged 30 years of age. The hosts' lineup included Latapy and Yorke, who played against the U.S. in that famous 1-0 qualifying win that boosted the Americans into their first FIFA World Cup some 19 years ago on Nov. 19, 1989. The U.S. qualified for the World Cup for the first time in 40 years and hasn't missed reaching the world's greatest sporting spectacle since.
Trinidad waited 16 years to finally qualify for the very first time, booking a spot at Germany 2006.
While both sides had their own motivation, Trinidad definitely showed it was the hungrier team, forcing the action down the flanks in the first half and getting off some dangerous shots at the U.S. goal.
But former Chivas USA goalkeeper Brad Guzan, currently with Aston Villa, was up to the task and then some, either catching or knocking away everything that came his way.
The Soca Warriors finally broke through in the 61st minute. Latapy brought the ball down the middle and sent it to the right side to Carlos Edwards, who took the ball toward the goal line. Edwards then chipped the ball to the onrushing Latapy, whose 13-yard left-footed shot hit the left post and pounded off Guzan's back into the goal. It was Latapy's 29th international goal in his 74 appearances. He also has nine qualifying goals in 38 games.
Altidore, who currently performs for Villareal, played an important role in the next two goals.
On the U.S. equalizer in the 75th minute, former Toronto FC midfielder Maurice Edu, now with Glasgow Rangers, pushed the ball ahead to Altidore, who possessed the ball on the left side of the penalty area before sending Charlie Davies a short cross and the former Boston College standout and current Hammarby IF player beat goalkeeper Clayton Ince from three yards. Davies had come on for former Real Salt Lake and D.C. United midfielder Freddy Adu in the 69th minute.
Only four minutes after the U.S. score, Altidore tugged at Makan Hislop's shirt and took him down to the ground as referee Walter Quesada whistled a penalty kick. Yorke converted to a lower left while Guzan dived the other way as the crowd cheered wildly at the Sunderland midfielder's 17th international goal in 61 matches.
As it turned out, Altidore had a chance to level the game from point-blank range in the 83rd minute, but his close-range header went wide left. Realizing he had missed a gold opportunity, Altidore put his hands up to his head in disbelief.
The young U.S. side will have another opportunity to impress Bradley in their final semifinal qualifier Nov. 19.
Trinidad? The Caribbean side certainly can clinch a spot in the confederation finals with a win over Cuba that day.
Michael Lewis is a contributor to MLSnet.com. This story was not subject to the approval of Major League Soccer or its clubs.