On 28 June 1999, Palmeiras won their first (and to date only) Copa Libertadores, beating Deportivo Cali on penalties. The win concluded Brazil's domination of the tournament in the 1990s, with six out of ten titles.
Palmeiras had to go through two Brazilian teams to reach the final, including defending champions Vasco da Gama in the Round of 16 and rivals Corinthians in the quarterfinals. They then beat River Plate over two legs in the semifinals to advance to the final. Meanwhile, Deportivo Cali reached the final over Colo-Colo, Bella Vista, and Cerro Porteño.
The final was played over two legs, with Deportivo Cali winning 1-0 at home thanks to a 42nd-minute goal from striker Víctor Bonilla. For the second leg, the teams met at the Estádio Palestra Itália in São Paulo, where a crowd of 32,000 gathered to watch.
After a scoreless first half, Palmeiras went ahead with a penalty kick in the 65th minute, but Deportivo Cali equalized five minutes later with a penalty kick of their own. Penalties would go on to decide the title, after Palmeiras forward Oséas Reis dos Santos scored the final goal of regulation in the 76th minute to level the series at one win each. From there, the match went into a shootout, which Palmeiras won 4-3.