Sean McFarlane, Zhelano Barnes and Kareen Manning all scored for Jamaica to lead it to a 3-0 victory over Suriname, while Andy Vaquero and Yordan Santa Cruz both scored in the final nine minutes to lift Cuba past Antigua and Barbuda 2-0.
The wins gave both six points atop Group B in the Caribbean U-20 finals, while Suriname and Antigua remained pointless with one game remaining for each. Two teams from both Groups A and B advance to next year's CONCACAF finals in Puebla, Mexico, in February, along with the best third-place team.
Haiti, which leads Group A with six points, therefore also clinched.
McFarlane put Jamaica ahead a minute before halftime, and Barnes doubled the advantage in the 65th.
The second goal came three minutes after Suriname goalkeeper Delano Stella had to leave the game. He initially appeared to injure himself in the 55th minute when he fell on his back on the ball. He continued but eventually had to be replaced by Sersinino Profijt in the 62nd.
Manning completed the victory in the 93d.
In the opening match, Vaquero broke the stalemate in the 81st and Santa Cruz tacked on the second in the 92nd.
Jamaica's victory makes it the fifth straight time it has qualified for the CONCACAF championship and 18th overall. Cuba reached the confederation championship for a second straight time and 11th overall.
Haiti, which beat Trinidad on Wednesday, will play in the finals for the first time since 2007.
The three, along with two more from the Caribbean, will join automatic North American qualifiers Canada, Mexico and the United States, as well as Central American entrants Costa Rica, El Salvador, Nicaragua and Panama in the 12-team CONCACAF finals.