After his playing career, Cheveldayoff joined the Denver Grizzlies of the International Hockey League for three seasons as an assistant to head coach Butch Goring.

Longtime Manitoba Moose general manager Craig Heisinger, a friend of Cheveldayoff's from their days with the Wheat Kings, was named as his assistant.

[2] On May 16, 2018, Cheveldayoff was named a finalist for the NHL General Manager of the Year Award after he guided the Jets to their best regular season record and to the Western Conference Finals for the first time ever.

In May 2021, the Chicago Blackhawks launched an internal investigation after two former players alleged they were sexually assaulted by video coach Brad Aldrich during the 2010 Stanley Cup playoffs.

[4] The findings of the investigation were released on October 25, revealing that Cheveldayoff, then an assistant general manager for Chicago, was part of a group of executives within the Blackhawks who knew of the allegations against Aldrich, but failed to file a formal police report.