Calvillo won three Grey Cup championships in 2002, 2009, and 2010, and named Grey Cup Most Valuable Player in 2002. He also won the CFL's Most Outstanding Player Award three times, in 2003, 2008, and 2009, which ties him for second all-time behind Doug Flutie. Calvillo announced his retirement on January 21, 2014. Calvillo was an assistant coach for the Alouettes from 2015 to 2017 and with the Toronto Argonauts in 2018.