Watkins would go on to record five straight 1,000-yard seasons between 2005 and 2009 while falling just short in 2010 with 970 after he missed five games due to injury. He won Grey Cup championships with the Alouettes in 2009 and 2010, making a critical 17-yard catch in the 2009 game to put the Alouettes in field goal range to kick the winning points. His 2011 season was curtailed due to injury where he only managed to catch 31 passes for 395 yards and three touchdowns. Nonetheless, he finished the season in second place on the Alouettes all-time receptions list at 515 catches, behind all-time franchise and CFL leader Ben Cahoon. Following the 2011 season, Watkins announced his retirement on January 31, 2012.