KINGSTON, Jamaica -- After Clint Dempsey scored the fastest U.S. goal in World Cup qualifying, the Americans played a listless game, lost to Jamaica for the first time and put pressure on themselves to win their home game against Jamaica next week.
Rodolph Austin and Luton Shelton scored on free kicks as the Reggae Boyz rallied for a historic 2-1 victory Friday night, their first win in 19 games against the Americans.
"Jamaica deserved that win. They were hungrier and they were more determined," U.S. coach Jurgen Klinsmann said. "We have to fix it now."
Jamaica (2-0-1) leads Group A with seven points at the halfway point, and the U.S. (1-1-1) dropped into a second-place tie with Guatemala (1-1-1), which overcame an early deficit to win 3-1 at home over Antigua and Barbuda (0-2-1).
"We have to do to do a better job with concentration," American goalkeeper Tim Howard said. "To give away six, seven free kicks in that area is not good enough."
The U.S. hosts Jamaica on Tuesday night at Columbus, Ohio.
"We need to figure out a way, whether it's more width, whether it's more crosses, whether it's just doing a better job of keeping the ball," Dempsey said.
Playing his first competitive match in three months, Dempsey put the U.S. ahead 35 seconds in. The 60th-ranked Reggae Boyz, who had been 0-10-8 against the U.S., rallied with goals in the 23rd and 62nd minutes on free kicks caused by fouls from Kyle Beckerman and Maurice Edu.
"Next game we have to limit the mistakes and create more chances," Edu said. "We are disappointed but we still have more games to play."
Jamaican fans ran onto the field when the match ended.
"It means a lot to me to beat the U.S. for the first time," said Shelton, who plays for Karabukspor in Turkey. "I cried after the game. I have never cried after such an important game. I believe our team is a very good team and to create history was sweet."
The top two nations advance to next year's six-nation regional finals, which will produce three qualifiers for the 2014 tournament in Brazil. The U.S. is not a dire situation yet, with home games against Jamaica and Guatemala, and a road match at Antigua.
"We will have to step it up a level and definitely have to watch their free kicks, because they were very dangerous obviously on the free kicks," Beckerman said.
Missing injured Landon Donovan (hamstring) and Michael Bradley (thigh), the 33rd-ranked U.S. was dominated in the midfield and dropped to 0-1-4 in qualifiers at The Office, as Independence Park is known.
The U.S. went ahead after Edu played a through pass to Herculez Gomez, whose initial shot and follow-up both were stopped by goalkeeper Dwayne Miller. The second shot rebounded to Dempsey, who scored from about 10 yards for his 28th international goal. He has scored in all three U.S. qualifiers this year.
Dempsey's previous match was a World Cup qualifier at Guatemala on June 12. Dempsey had held the record for fastest U.S. goal in a qualifier when he scored 53 seconds in against Barbados in 2008.
"Maybe we were leading too early," Klinsmann said.
Dempsey moved from Fulham to Tottenham on Aug. 31 just before the transfer deadline closed and had missed the start of the English Premier League season while his club status was sorted out.
Jamaica increasingly dominated the midfield, and the Reggae Boyz tied the score after a late tackle by Beckerman on Austin gave Jamaica a free kick about 28 yards out. Austin took the kick and his shot deflected off Beckerman's right foot on the defensive wall and past Howard.
Beckerman was replaced in the 58th minute by Danny Williams, who made his first competitive appearance for the U.S. Williams also had been eligible to play for Germany.
Howard went down after colliding with Shelton about eight minutes into the second half, and Jamaica took the lead after Austin was fouled by Edu. Shelton's free kick from about 25 yards went in just inside the post as Howard dived to his right, extending his Jamaican record with his 34th international goal.
"We didn't use the ball well," Howard said. "The field wasn't great, but those are not good enough."
Right back Steve Cherundolo was scratched because of a strained right calf. Captain Carlos Bocanegra, who transferred last week from fourth-tier Glasgow Rangers to second-tier Racing Santander, was benched.