Jamaica stunned Chile 2-1 in their pre-Copa America Centenario friendly in Vina del Mar on Friday.
Juan Antonio Pizzi's Chile, which is looking to defend its Copa title in the United States, had chances but was 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 was left to rue the misses at home.
The side gets another chance to find form with a clash against Mexico on Wednesday, just days before a tough Copa opener with Argentina.
Jamaica, meanwhile, will carry its winning form into its 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 defense down the right before squaring for Giles Barnes, who missed a glorious chance from the middle of the penalty area.
After the home side went close from a corner in the 12th minute, Jamaica was 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 equalizer.
Jean Beausejour curled an effort wide just before the break as Jamaica took a one-goal advantage into halftime.
Beausejour pushed a shot wide in the opening minute of the second half before Mauricio Isla went close with a volley.
The home side was dominant after the interval and Mauricio Pinilla almost leveled, only for his header to be kept out by a strong save by substitute keeper Duwayne Kerr.
Chile would be punished for its 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 home side finally scored, with Kemar Lawrence clearing a ball straight into Castillo, but the visiting side held on.