- In September 2025, Flamengo won 2-1 in Rio de Janeiro before Estudiantes responded with a 1-0 victory in La Plata; with the tie level at 2-2 on aggregate, Agustín Rossi settled it with two saves in the penalty shootout.
- The 'Mengão' went on to lift the trophy in Lima, while the 'Pincha' bowed out with Eduardo Domínguez promising to “turn the pain into something positive”.
The only previous meeting between Flamengo and Estudiantes in the CONMEBOL Libertadores before 2026 lasted 180 minutes and eight penalty kicks. It came in the 2025 Quarter-finals, in September, and ended with the 'Mengão' on their way to a fourth continental crown and the 'Pincha' eliminated without losing the tie over the 90 minutes. It is the most recent knockout-stage precedent ahead of the Semifinal that will bring them together again on 15 and 22 October.
The first leg, played at the Maracanã on 18 September last year, began to take shape before many supporters had even settled into their seats. After just 16 seconds, Pedro pressed high, won the ball back, combined with Gonzalo Plata and finished past Fernando Muslera: it was the fastest goal Flamengo had ever scored in the history of the CONMEBOL Libertadores. In the eighth minute of the first half, Guillermo Varela volleyed in an Ayrton Lucas cross to make it 2-0. Flamengo became only the fourth Brazilian club to score twice in the opening ten minutes of a knockout-stage match.
Estudiantes waited for their moment and found it late on. In the 45th minute of the second half, Guido Carrillo struck a loose ball that took a deflection off Léo Pereira and pulled one back to make it 2-1, leaving the tie wide open. “It was about waiting for our moment. At home, it will be different,” said Eduardo Domínguez, now head coach of Atlético Mineiro.
The second leg, played at Estadio UNO on 25 September, was the match Estudiantes had promised. In the final move of the first half, Gastón Benedetti collected a long pass from Santiago Núñez and unleashed a left-footed strike from outside the box that slipped past Rossi. It was 1-0 on the night and 2-2 on aggregate. In the second half, Pedro came close to equalising with an effort that Facundo Rodríguez cleared off the line, Saúl struck the post and Benedetti found the net again, only for the goal to be ruled out for offside. The tie went to penalties.
Flamengo took the first kick. Jorginho and Luiz Araújo converted; José Sosa kept Estudiantes in contention, but Rossi saved Benedetti’s second attempt. Jorge Carrascal, Edwuin Cetré and Léo Pereira then scored, before the goalkeeper stepped up again to deny Santiago Ascacíbar and seal a 4-2 shootout victory.
Filipe Luís recalled it this way: “When it went to penalties, he told me: ‘Leave it to me. I made a mistake earlier, and now I’m going to take us through.’ I believed him, he made two great saves and we managed to qualify.” Rossi put it in his own words: “I know I had some responsibility for the goal during the match. I told my team-mates I was going to help them in the shootout. I was fortunate enough to save two penalties and decide the tie.”
Domínguez did not hide either the pain or the pride. “I’m left with the performance the team produced against an opponent of such quality. The tie finished level, and I think what the players did was extremely valuable,” he said that night. Estudiantes went on to win the 2025 Torneo Clausura and the Trofeo de Campeones, returned to the CONMEBOL Libertadores and reached the 2026 Semifinals after eliminating Corinthians.
Flamengo, meanwhile, turned that penalty shootout into the starting point of a title run. They eliminated Racing in the Semifinals with a 1-0 win at the Maracanã and a 0-0 draw in Avellaneda, before beating Palmeiras 1-0 in Lima on 29 November through Danilo’s header from a Giorgian De Arrascaeta corner. Rossi, who finished the tournament with eight clean sheets in 12 matches before the Final, reached six penalty saves in CONMEBOL Libertadores shootouts since 2018 this year, second only to Sergio Romero’s seven.
The head-to-head record between the two sides in the competition now stands at four matches: the two from that knockout tie and the two from the 2026 Group Stage. They drew 1-1 in La Plata on 29 April, with goals from Luiz Araújo and Carrillo, before Flamengo won 1-0 at the Maracanã on 20 May through Pedro. That leaves the 'Mengão' with two wins, the 'Pincha' with one, and one draw. And there has been one constant: every meeting has been decided by a single goal or ended level. With the first leg in La Plata, the Semifinal promises drama right to the end.
