He has coached professional football since 2000 and won a Grey Cup championship with the CFL's Calgary Stampeders in 2008 and with the Edmonton Eskimos in 2015.

[11] The following day, he joined the CFL's Winnipeg Blue Bombers to be their Special Teams Coordinator for the 2013 season.

Shortly after winning the Grey Cup, Chris Jones became the General Manager and Head Coach of the Saskatchewan Roughriders for the 2016 season.

He brought most of his coaching staff from Edmonton to Saskatchewan, including Dickenson as Special Teams Coordinator.

In January 2019, Jones resigned as Saskatchewan's General Manager and Head Coach to join the NFL's Cleveland Browns.

[21] Saskatchewan ultimately lost at home in the Western Final to the eventual Grey Cup champions, the Winnipeg Blue Bombers.

[23] With Dickenson as Saskatchewan's Head Coach in 2021, the Riders finished second in the West Division, won their first home playoff game at new Mosaic Stadium, but once again lost to the eventual Grey Cup champion Winnipeg Blue Bombers in the Western Final.

Saskatchewan started the 2022 season under Dickenson 4-1, but ultimately finished with a disappointing 6-12 record and failed to make the playoffs for the first time since 2016.