In a result that will be viewed as a catastrophe for soccer in the United States, Trinidad took all three points via an Omar Gonzalez own goal and a superb strike from Alvin Jones.
US star Christian Pulisic pulled a goal back in the second half, but the increasingly desperate Americans were unable to find another to rescue their hopes.
Their exit was confirmed by results in Tuesday’s other CONCACAF qualifiers, where Panama booked their place at the World Cup for the first time with a 2-1 win over Costa Rica in Panama City.
Honduras then snatched fourth place in the table with a 3-2 win over Mexico, who had already qualified.
The Hondurans will now face Australia in a two-legged playoff next month for a place in the finals.
But the shock of the night was without a doubt the US failure at the final hurdle.
Bruce Arena’s side had needed only a draw at the Ato Boldon Stadium to be virtually certain of securing at least a playoff spot.
After thrashing Panama 4-0 last Friday, the Americans had arrived in the Caribbean confident of securing the result needed to extend a proud record of qualifying for every World Cup since 1990.
Yet it started to go wrong for Arena’s men after 17 minutes when Gonzalez’s sliced clearance looped high and over the stranded Tim Howard to put Trinidad and Tobago 1-0 up.
It got worse just after the half-hour mark when Alvin Jones produced a goal out of nothing to double the home side’s lead.
Gathering the ball on the right flank, roughly 35 yards from goal, Jones let fly with a ferocious shot which flew past Howard to make it 2-0.
Pulisic then gave the US hope with a deflected shot soon after half-time to make it 2-1.
As the changing scores in the other games began to filter through to the American ranks, the US became increasingly desperate.
But despite the desperation, Trinidad and Tobago held firm for a famous win that is likely to trigger a prolonged inquest in US soccer.