Born in Rio de Janeiro, Oswaldo de Oliveira became the first team coach for Corinthians in 1999 when Vanderlei Luxemburgo left the club to take the Brazil National Team manager role.
Oliveira led the club to win the São Paulo State Championship and the Brazilian Série A that same year.
In the 2013 season, he led Botafogo to 4th place in the league, qualifying the team for the Copa Libertadores.
After the 2013 season, Oliveira was hired by fellow Brazilian side Santos FC.
In 2015, he coached Palmeiras, which made him the first manager to have worked with all four main teams of São Paulo (Corinthians, Palmeiras, Santos and São Paulo) and four main teams of Rio de Janeiro (Botafogo, Flamengo, Fluminense and Vasco).