For the first time in 19 meetings between the two teams, the Americans lost to Jamaica as they moved behind the Reggae Boyz in Group A.
Now they have another first. But it's not the kind they would want.
The U.S. team suffered its first loss to Jamaica in 19 games between the two nations after the Reggae Boyz bounced back from an early deficit to hand Jurgen Klinsmann's squad a 2-1 defeat at National Stadium in CONCACAF World Cup qualifying.
Clint Dempsey set an American qualifying record by scoring 36 seconds into the match, but the visitors would go the rest of the 89-plus minutes without a goal. Jamaica scored twice on free kicks, from Rodolph Austin and Luton Shelton on either side of the half for the comeback win.
The U.S. entered the match with 10 wins and eight draws in the all-time series between the teams.
"Jamaica deserved that win," coach Klinsmann said after the match. "They were hungrier and they were more determined, and that's how they came off the field as the winning team."
The U.S. (1-1-1) now sits behind Jamaica (2-0-1) in Group A after entering the match in first place due to better goal differential. The two teams will meet again on Tuesday in Columbus.
"We expected a very difficult game, we were aware of the Jamaican team and we respected them," Klinsmann said. "And we have to take it the way it is now."
The Americans couldn't have asked for a better start while playing in a party-like atmosphere on the Caribbean island as their star player stepped up in the opening seconds.
Dempsey was supposed to be rusty after a summer of transfer drama at Fulham before moving to Tottenham in the closing hours of last Friday's transfer deadline, but he was in Klinsmann's starting lineup, which turned out to be the right decision.
Dempsey opened the scoring after Maurice Edu found Herculez Gomez down the right side. Gomez had a path to the goal but saw his first shot saved by keeper Dwayne Miller and the second blocked by a defender before Dempsey put the rebound into the back of the net.
Dempsey, who scored 53 seconds into the match against Barbados in the previous World Cup qualifying cycle, set a U.S. qualifying record by scoring 36 seconds into the match. He also moved into a tie for fourth all-time in the U.S. with eight World Cup qualifying goals.
Dempsey has scored in three straight qualifying games, but Klinsmann's men could have used one more.
"It's just getting back to that intensity and playing on a high level," Dempsey said. "It's my first game back and a lot of these other guys have been playing quite a few games. I just have to hit the ground running and hopefully I'll be better next game."
Just as the case after Dempsey scored in the first half against Guatemala in the United States' previous qualifier last June, the Americans would concede the tying goal in an unlikely circumstance. Unlike their match in Guatemala, they couldn't walk away with a draw.
Jamaica couldn't get close to the U.S. net throughout the night, but perfectly taken free kicks by Austin and Shelton from well outside the box had Klinsmann's men, and the nearly sold-out crowd, completely shocked.
In the 24th minute, Austin drove a low shot through the U.S. wall, leaving Howard with no chance to make a play. In the 66th minute it was deja vu for the U.S. as Shelton beat Howard from distance.
"That's the risk you take when you give free kicks away in dangerous positions," Howard said.
Klinsmann entered the night looking for a positive result and did not view the match as a must-win with plenty of qualifying games left to play. But he may have to reevaluate his thinking heading back to the United States next week.
The U.S. was riding high after defeating Mexico at Azteca in August, but that was just a friendly.
"It's important that we get three points in the next game," Dempsey said.