Jamaica stunned Chile 2-1 in their pre-Copa America Centenario friendly in Vina del Mar on Friday.
Juan Antonio Pizzi's Chile, who are looking to defend their Copa title in the United States, had their chances but were punished at the Estadio Sausalito.
Clayton Donaldson's first-half opener and Joel Grant's goal after the break sealed the win for Winfried Schafer's men before Nicolas Castillo needed some luck to pull a late one back with his first international goal.
Chile had numerous opportunities, particularly before going 2-0 down, but were left to rue their misses at home.
They get another chance to find form with a clash against Mexico on Wednesday, just days before their tough Copa opener with Argentina.
Jamaica, meanwhile, will carry their winning form into their Group C clash against Venezuela on June 5.
A lively opening led to chances at both ends as Eduardo Vargas fired wide from range before Jamaica should have taken a third-minute lead.
Garath McCleary ran at the Chile defence down the right before squaring for Giles Barnes, who missed a glorious chance from the middle of the penalty area.
After the hosts went close from a corner in the 12th minute, Jamaica were perhaps unlucky not to win a penalty at the other end.
Donaldson appeared to be brought down by goalkeeper Johnny Herrera, but no spot-kick was awarded.
Jamaica took the lead in the 36th minute through Donaldson, as the dangerous McCleary cut back for the Birmingham City striker to poke in from close range.
Alexis Sanchez had a free-kick tipped over and Gary Medel a brilliant overhead kick cleared off the line as Chile pushed for an equaliser.
Jean Beausejour curled an effort wide just before the break as Jamaica took their one-goal advantage into half-time.
Beausejour pushed a shot wide in the opening minute of the second half before Mauricio Isla went close with a volley.
The hosts were dominant after the interval and Mauricio Pinilla almost levelled, only for his header to be kept out by a strong save by substitute keeper Duwayne Kerr.
Chile would be punished for their profligacy as Barnes' cross from the right was headed in by Grant in the 53rd minute.
Medel poked wide and Sanchez missed the target from 25 yards before the latter set up substitute Edson Puch, who somehow volleyed wide from an angle as Chile's chances continued to flow.
Jamaica somehow scrambled two Chile chances clear before the hosts finally scored, with Kemar Lawrence clearing a ball straight into Castillo, but the visitors held on.