The airline was established on 30 November 1995 and started operations in 1997.
On February 19, 2014, Skymaster along with BETA Cargo were fined by CADE (Brazilian antitrust court) a combined 83 million reais (35 million USD), for running a cartel that hampered competition and drove up bid prices of procurements by the country's state-owned postal service Correios.
On 7 March 2001, a Skymaster Airlines 707-320C, registration PT-MST, landed hard on Runway 09R, São Paulo-Guarulhos International Airport in São Paulo, Brazil. As a result of the landing the undercarriage failed, damaging all four engines and injuring three people. The aircraft was subsequently written off.