In 2009, Trestman led the Alouettes to win the 2009 Grey Cup, winning with a thrilling field goal with no time left on the clock. After the season, it was announced that he was signed through the 2012 season as the head coach. Trestman also led the Alouettes to a Grey Cup win in 2010. Trestman is the only coach in Alouettes history to win back-to-back Grey Cups. Under Trestman's guidance, Alouettes QB Anthony Calvillo won back-to-back MVP awards in 2008 and 2009.