Flamengo and Estudiantes meet again, this time in the Libertadores semifinals

Some matchups no longer surprise anyone, and this is one of them. Flamengo and Estudiantes are set to meet again in the Copa Libertadores, this time in the semifinals, and it feels like two rivals who already know each other by heart. It's no coincidence: Estudiantes was the team Flamengo eliminated in the 2025 quarterfinals, and also the one it faced twice in the group stage of this 2026 edition.

The series kicks off Thursday, October 15 in La Plata, with the return leg a week later at the Maracana, with a spot in the final on the line. And if anything has become clear over the past few years, it's that Argentine clubs have turned into an almost mandatory stop on Flamengo's continental path: Central Cordoba, Estudiantes and Racing in 2025, Lanus in this year's Recopa (the Granate beat them right at the Maracana to claim the title), and now Estudiantes again.

The overall head to head record in the Copa favors Flamengo: in 29 matches against Argentine opponents, it has won 15, drawn 10 and lost just 4, scoring 60 goals and conceding 34. Those numbers carry weight, though soccer has its own way of reminding everyone that history also gets written in the moment.

A result Estudiantes remembers fondly

To find the first time Estudiantes beat Flamengo in a two-legged tie, you have to go back to 1994, during the Supercopa, when the La Plata side had just been relegated to the Nacional B. The first leg at the Maracana ended 0-0, and in La Plata, Estudiantes made history with a 2-0 win thanks to headed goals from Javier Ferreira and Alejandro Mendez. On that roster, coached by Miguel Angel Russo and Eduardo Manera, played a 19 year old named Juan Sebastian Veron.

Before that series, Flamengo had won all three previous meetings between the clubs (1988, 1991 and 1992). A long silence followed until 2025, when they met again, this time in the Libertadores quarterfinals: Flamengo won 2-1 at the Maracana, Estudiantes answered with a 1-0 win in La Plata, and it all came down to penalties, where Argentine goalkeeper Agustin Rossi, wearing the Brazilian club's jersey, stopped two shots and sent Flamengo through to the semifinals. That Flamengo side went on to win the title.

In 2026, the rematch came quickly: both teams landed in the same group, drew 1-1 in La Plata and Flamengo won 1-0 in Rio. The curious part is that while Flamengo dominates the overall series, Estudiantes rules at home: in six matches played in La Plata, Estudiantes has won two, drawn three and lost just one. Flamengo, meanwhile, remains unbeaten at home against Estudiantes, with four wins and two draws.

A Flamengo that has made this a habit

Flamengo arrives as the defending champion and still unbeaten in this 2026 Libertadores. It won Group A with 16 of 18 possible points, knocked out Cruzeiro in the round of 16 and Independiente del Valle in the quarterfinals (2-0 in Quito, 1-1 at the Maracana). This will be its eighth Libertadores semifinal in history, and its fifth since 2019, a stat that speaks to a dominance sustained over time.

Estudiantes, for its part, arrives after eliminating Corinthians with a 1-1 draw in La Plata and a 1-0 win in Sao Paulo. It's no longer playing for a spot among the final four, now the prize is the final itself. And while the overall numbers lean one way, the history between these two clubs shows that when Flamengo takes on Estudiantes, surprises are never off the table.