In 2009, Calvillo added to his club records while reaching more CFL milestones. On July 23, 2009, he surpassed Canadian Football Hall of Famer Ron Lancaster's 334 career touchdown passes to move into second place all time. He sat out two games during the regular season, but still accumulated 4639 yards while posting a remarkable 72.0% completion rate, the second best single-season completion rate in CFL history behind Dave Dickenson's 73.98% mark set in 2005. Calvillo led Montreal to a 16-point fourth quarter comeback victory in the 97th Grey Cup on Nov. 29, when the Alouettes defeated the Saskatchewan Roughriders 28-27 on a last-second field goal known as the "13th Man" finish.