Jamaica's first ever win over the US was thoroughly deserved after they fought back with determination from the early blow of Clint Dempsey's first minute goal.
The two sides meet again in Columbus, Ohio on Tuesday and while both are expected to advance from group one into the six-team final qualifying phase, the pressure is on Juergen Klinsmann's US team.
Having only drawn their opening game, away to Guatemala before beating Antigua and Barbuda, the US are now second in the group on four points, trailing Jamaica by three.
Dempsey, who recently moved from Fulham to Tottenham, put the US ahead in just the 36th second, slotting home after Herculez Gomez's shot was blocked on the line.
But the 'Reggae Boyz' drew level in the 24th minute when Rodolph Austin, who also plays in England with second tier Leeds United, struck a low free-kick which took a slight deflection off Kyle Beckerman in the US wall.
It was a scrappy battle for the rest of the first half with the Americans struggling to retain possession in midfield against the hard-working Caribbeans.
Dempsey went close again just before the break when he slid in to meet a Michael Parkhurst cross but Jamaica keeper Dwayne Miller got down well to save.
After the interval, Austin forced American keeper Tim Howard into action with a stinging shot from a full 30 yards out and as the game wore on, the home side grew in confidence.
Jamaica got their reward in the 62nd minute and in spectactular fashion with Shelton unleashing a thundering free-kick which flew into the top corner of Howard's goal.
At the half-way stage in the third round of qualifying in North and Central America and the Caribbean, Mexico are the only team with a 100 per cent record after they picked up a third win in three games with a 2-0 victory at Costa Rica in group B.
Both Mexican goals came from corners with Carlos Salcido putting 'El Tri' ahead two minutes before the break and then Jesus Zavala adding the second in the 52nd minute.
Guatemala suffered a scare against Antigua and Barbuda, falling behind to a Peter Byers goal in the 38th minute but Carlos Ruiz scored twice before Dwight Pezzarossi slid in at the back post in injury time to wrap up a 3-1 win.
Canada are the surprise leaders in group C, on seven points, after a Dwayne De Rosario goal gave them a 1-0 win in Toronto over Panama, who are now a point behind the Canadians and two ahead of Honduras.
De Rosario's record 20th goal for his country came in the 77th minute, as he reacted to a quick free-kick by Atiba Hutchinson to fire past Panama keeper Jaime Penedo.
"It was good to score, good to get the points and the atmosphere was fantastic. I thought the first half was some of the best we've played and I said at halftime that the goal would come," said Canada head coach Stephen Hart.
Honduras remain in the chase though after they picked up their first win in group C with a 3-0 victory over Cuba in Havana - Jerry Bengtson (31), Victor Bernandez (63) and Marvin Chavez (90+2) getting the goals.
Guyana's chances of making it to the final six stage of the qualifying competition are remote but they showed signs of their progress with a 2-2 draw in El Salvador.
Treyon Bobb equalised twice for Guyana after goals from Isidro Gutierrez and Osael Romero for an El Salvador team who are two points behind Costa Rica in group B.
Friday's fixtures will now be reversed for Tuesday's return games.
Three teams from CONCACAF's North and Central America and Caribbean region qualify automatically for the 2014 World Cup finals in Brazil. The fourth-placed team from the last phase also has a chance to qualify if they win a play-off against the winner of Oceania's qualifying.