The Brazilian outfit kicked off their campaign with a 3-2 win over Velez Sarsfield last time out, while the visitors drew their opening game 2-2 with LDU Quito.
Flamengo recorded an important victory in the first game of their Copa Libertadores campaign, when they travelled to Argentina to take on Velez Sarsfield.
The hosts took the lead on two separate occasions through Lucas Janson, but goals from William Arao and Gabriel Barbosa drew Flamengo level before Giorgian de Arrascaeta netted the winning goal with 10 minutes to go.
That cemented their spot at the top of the Carioca Serie A table, meaning they now go into the semi-final stage to again take on Volta Retonda, who finished fourth.
However, their attention will remain on the Copa Libertadores, as they look to boost their chances of lifting the trophy for the third time in their history.
The most recent glory came in 2019, as a late Barbosa brace fired Flamengo to a 2-1 victory over River Plate in the final.
They take on a Union La Calera side who will be looking to put their first win of the campaign on the board after a draw last time out.
They suffered a narrow defeat last time out when they returned to league action, as a Marcelo Larrondo goal in the 76th minute fired O'Higgins to a 1-0 victory.
Luca Marcogiuseppe's side will now look to bounce back from that defeat with a win which would see them leapfrog Flamengo in the group and move into the top two, as they aim to book their spot in the final 16.
Gabriel Barbosa was the hero in Flamengo's 2019 Copa Libertadores victory, and he will be a key man again this year, leading the line for Rogerio Ceni's side.
Meanwhile, Vitinho will be pushing for a starting spot after his winning goal in the last league game.
The core of that 2019 side will again feature on Tuesday, with De Arrascaeta, Ribeiro, Gerson, William Arao and Felipe Luis all still playing key roles.
Luca Marcogiuseppe rested the majority of his key players for the recent league game against O'Higgins, with Tuesday's important game in mind.
Vilches will lead the line, having netted a brace in the opening draw with LDU Quito.
Flamengo possible starting lineup:
Alves; Isla, Arao, Henrique, Luis; Diego, Gerson; Ribeiro, De Arrascaeta; Henrique, Barbosa
Union La Calera possible starting lineup:
Arias; Ramirez, C. Vilches, Garcia, Oyanedel; Reyes, Castellani, Wiemberg; Vargas; A. Vilches, Rivero
We say: Flamengo 2-0 Union La Calera
The Brazilian giants should have too much for their opponents on Tuesday, and we see them building on their strong form to kick the Copa Libertadores campaign off with back-to-back victories.
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