Throughout his career he played for several Paraguayan clubs such as Guaraní (where he was part of the 1984 team that won the Paraguayan Championship), Olimpia and Cerro Porteño, and for Argentine club Chaco For Ever. Rolando Chilavert was part of the Paraguay national football team that competed in the 1986 FIFA World Cup. He played as an attacking midfielder and was known for his creativity and precision in the passes.
After retiring as a player, Chilavert started a coaching career that included teams such as Guaraní and Sol de América (from Paraguay), The Strongest (from Bolivia), and also the youth divisions of the Paraguay national team (Under-17 and Under-20).
