He was the 25th head coach of the Winnipeg Blue Bombers. He became acting head coach after Dave Ritchie was let go part way through the 2004 season, and was named the head coach for the 2005 season. After the 2005 season he was let go, as the team finished in last place in the Western Conference. He was previously an assistant coach with the Bombers and before that the coach of the Saskatchewan Roughriders. With the Riders, he finished with a losing record in each of his three seasons as coach, but was able to lead the team on a run to the Grey Cup final in 1997, before losing to the Toronto Argonauts. Daley won the Grey Cup as an assistant with Calgary.
In 2007, Daley was hired by the CFL as a league official to work as senior director of officiating development. In 2009, Daley was hired by the Edmonton Eskimos as the team's Defensive Coordinator and Defensive Line Coach. Shortly following the 2009 season on December 9, 2009, Daley later resigned from his position.
On February 18, 2010, it was announced that Daley had re-joined the Saskatchewan Roughriders, this time as their special teams coordinator. It was announced on January 14, 2011 that his contract would not be renewed by the Roughriders.
On February 3, 2011, it was announced that Daley had joined the Hamilton Tiger-Cats' coaching staff as their special teams coordinator.