Trinidad and Tobago beat the United States 2-1 in the team's final Hexagonal World Cup qualifier, meaning the Americans will miss out on the game's biggest tournament in Russia in 2018.
The result, combined with wins from Panama and Honduras, leaves the U.S. in fifth in the qualifying table, outside of the automatic and playoff spots on offer for the top-four finishers.
Bruce Arena picked the same XI that secured a huge 4-0 win against Panama on Friday night, knowing that three points would seal an automatic berth in Russia.
The game got off to a slow start on a pitch that had come under intense scrutiny in the days ahead of the match because it was waterlogged as recently as Monday.
And it was the visitors that got on the scoreboard first, after Omar Gonzalez deflected a 17th minute cross that looped over Tim Howard and into the U.S. goal to give Trinidad a 1-0 lead.
Less than a minute later, the referee waved off a Trinidad penalty shout against Gonzalez when it looked like one might have been given.
However, Trinidad found a second in the 36th minute when Alvin Jones smashed a swerving shot from the right flank past Howard to give the hosts a 2-0 advantage at the break.
Christian Pulisic gave the U.S. the perfect start to the second half, firing home from just outside the penalty area just after kickoff to make it 2-1.
The U.S. were fortunate to have a second potential penalty waved off after DeAndre Yedlin took Jones down in the area.
Chasing an equalizer, Michael Bradley set up half-time substitute Clint Dempsey from a set piece, but the Seattle Sounders forward's first-time shot from 18 yards away was saved by Adrian Foncette in the Trinidad goal.
Dempsey was denied again just past the 80-minute mark after nice give and go with Pulisic, but Foncette was up to the task again and denied the U.S. on the doorstep yet again.
Honduras beat Mexico 3-2 and Panama scored a last-gasp winner to beat Costa Rica 2-1 to help both teams leapfrog the U.S., meaning Arena's team is the first American group not to make the World Cup since 1986.