The U.S. and Jamaica meet again Tuesday at Columbus, Ohio. The top two nations advance to next year's six-nation regional finals, which will produce three qualifiers for the 2014 tournament in Brazil.
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 Independance 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.
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.
Dempsey nearly scored in the 44th minute. Michael Parkhurst crossed and Dempsey's sliding shot was stopped by Miller was a sprawling save.
Howard went down after colliding with Shelton about 10 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 rightl, extending his Jamaican record with his 34th international goal.
Right back Steve Cherundolo was scratched because of a strained right calf, further depleting a the U.S. lineup. Captain Carlos Bocanegra, who transferred last week from fourth-tier Glasgow Rangers to second-tier Racing Santander, was benched.
Geoff Cameron and Clarence Goodson were paired in central defense, with Parkhurst at right back and Fabian Johnson at left back.