Leônidas started his career at São Cristóvão. He then played for Carioca side Sírio e Libanez, where he was coached by Gentil Cardoso. When Cardoso left to coach Bonsucesso, he brought Leônidas with him. Between 1931 and 1932, he played for Bonsucesso before joining Peñarol in Uruguay in 1933. After one year, da Silva returned to Brazil to play for Vasco da Gama. He helped them win the Rio State Championship. After playing in the 1934 World Cup, he joined Botafogo and won another Rio State Championship in 1935. The following year, he joined Flamengo, where he stayed until 1941. Once again, in 1939, the team won the Rio State Championship. He was also at the forefront of the movement against prejudice in football, being one of the first black players to join the then-elitist Flamengo team.