- Flamengo and Estudiantes have played 12 official matches, with five wins for the Brazilian side, two for the Argentine club and five draws.
- After meeting in the 2025 Quarter-finals and the 2026 Group Stage, they will face each other again for a place in the CONMEBOL Libertadores Final.
Flamengo and Estudiantes will cross paths once again in the CONMEBOL Libertadores. The 2026 Semi-finals will bring together two clubs with a shared history that began in the 1988 Supercopa and, after more than three decades without an official meeting, has added four more matches across last season and the current campaign.
The overall record from their 12 encounters favours the ‘Mengão’, who have claimed five victories compared with two for the ‘Pincha’, alongside five draws. The Brazilian side also hold the advantage in goals scored, with 13 for and eight against. Estudiantes, however, have a precedent to fuel their belief: they have already eliminated Flamengo in a continental knockout tie.
The first chapter was written in the Round of 16 of the 1988 Supercopa. After a 1-1 draw at the Estadio José Amalfitani, with Oscar Antonio Gissi scoring for the ‘Pincha’ and Bebeto for the Brazilian side, Flamengo secured a 3-0 victory at the Maracanã through goals from Luis Henrique, Renato Gaúcho and Bebeto. The 4-1 aggregate win sent them through to the Quarter-finals, where they would suffer a heavy defeat against Nacional of Uruguay.
That tie marked the beginning of a run in which the Brazilian side won the first three knockout meetings between the clubs. In 1991, again in the Round of 16, a 1-1 draw earned by the Argentine side in Brazil left the contest finely poised, but Flamengo claimed a 2-0 victory away to Estudiantes thanks to goals from Zinho and Gaúcho. The ‘Mengão’ would then bow out in the following round against River Plate, who prevailed on penalties at the Maracanã.
A year later, this time in the Quarter-finals, Flamengo once again advanced. They won 1-0 at home, with Gaúcho again finding the net, before protecting their advantage with a 1-1 draw in La Plata. In the Semi-finals, Racing Club secured a place in the decider after a thrilling tie that was settled by Alfredo Graciani’s goal at ‘El Cilindro’ in Avellaneda.
The ‘Pincha’ recorded their first victory in the Round of 16 of the 1994 Supercopa. Following a goalless draw in Brazil, Estudiantes made home advantage count with a 2-0 win to overcome the Rio de Janeiro side for the first time. In addition to securing qualification, they completed the tie without conceding, a record that remains one of their fondest memories of this fixture. Despite beating Cruzeiro in the first leg of the Quarter-finals through a Juan Sebastián Verón goal, the ‘Pincha’ would eventually be eliminated at that stage.
More than two decades passed before the two sides met again, in the Quarter-finals of the 2025 CONMEBOL Libertadores. After eliminating Cerro Porteño, Estudiantes reached the last eight to face a Flamengo side that had knocked out Internacional. The first leg at the Maracanã began like a nightmare for the ‘Pincha’: Pedro scored inside the opening minute before Guillermo Varela made it 2-0 before the ten-minute mark. Estudiantes, however, showed their competitive edge and pulled one back through Guido Carrillo in the 46th minute of the second half.
The second leg was a very different story. Chasing a comeback, the ‘Pincha’ went after the win from the outset, applying constant pressure on ‘Fla’ on a brilliant night for Gastón Benedetti, who scored to make it 1-0 and level the tie on aggregate in first-half stoppage time. Roared on by their supporters on a classic Copa night, Estudiantes caused Flamengo plenty of problems, with the Brazilian side forced to hold firm and take the tie to a penalty shootout.
Agustín Rossi proved decisive in the shootout as the Brazilian side secured their place in the Semi-finals. Benedetti, one of the standout performers on the night, missed his penalty, while Santiago Ascacíbar — now at Boca — also failed to convert the fourth kick. Flamengo would go on to eliminate Racing in the Semi-finals before lifting the CONMEBOL Libertadores trophy against Palmeiras in Lima.
The 2026 Group Stage brought the two sides together again in Group A. They drew 1-1 in La Plata on Matchday 3, with Guido Carrillo and Luiz Araújo finding the net, before Flamengo claimed a 1-0 victory in Brazil on Matchday 5 through a Pedro goal. ‘Fla’ finished top of the group, while Estudiantes advanced as runners-up thanks to Mikel Amondarain’s dramatic 45’+3’ goal against Independiente Medellín. Amondarain now plays for Bologna in Italy.
Those recent results extended the ‘Mengão’s unbeaten home record against Estudiantes: across six matches, they have recorded four wins and two draws. In Argentina, however, the balance favours the ‘Pincha’, with two victories, three draws and just one defeat. Their head-to-head history will now feature a Semi-final tie for the first time. Estudiantes will look to repeat the qualification they achieved in 1994, while Flamengo will aim to extend their advantage in the direct meetings between the sides. After four matches across 2025 and 2026, they will meet again with an even bigger prize at stake: a place in the Final and the chance to take the final step towards ‘Eternal Glory’.
