In 2004, Santana successfully kept Vasco da Gama from relegation to the second division of Campeonato Brasileiro in his fourth stint as club's head coach. A year later, he was hired by Flamengo to also save them from relegation, which he did successfully. Having established a reputation as an "escape artist" capable of rescuing teams from relegation, he returned to Flamengo in 2007 with the same goal. He not only prevented relegation, but lead the Rio state club to a surprising third place finish to qualify for the 2008 Copa Libertadores.