On December 3, 2014 Calgary Stampeders general manager and head coach John Hufnagel announced that he would hand over the head coaching duties to Dickenson for the 2016 season. Dickenson led the team to a franchise record for points in a season with a 15-2-1 record in 2016. The Stampeders were also unbeaten over a 16-game stretch, which was a single-season league record. He also became the first rookie head coach in the Canadian Football League to win 14 games and also had the second highest point total in league history (one behind the 1989 Edmonton Eskimos). The team also finished with a perfect 9-0 home record, which was the third such instance in team history. Because of all his success Dickenson won the Annis Stukus Trophy for coach of the year. On January 20, 2017 Dickenson and the Stampeders agreed to a 3-year contract extension through the 2020 CFL season.