[2] Prior to being elected to public office, Cheveldayoff worked with Western Economic Diversification as a senior business advisor.
[citation needed] Cheveldayoff's first run for political office came in the 1993 Canadian federal election as a member of the Progressive Conservative Party in the riding of The Battlefords—Meadow Lake.
[11] While Cheveldayoff called himself a "centrist" and "very much a moderate" at the outset of the race, he drew scrutiny throughout the campaign for his stances on social issues.
[12] The same month, Cheveldayoff received the endorsement of a national anti-abortion lobbying group, who rated him the most "pro-life" of all leadership candidates.
[13] Cheveldayoff said that he would support "anything that emphasizes that life begins at conception", and stated that not even rape victims should have legal access to abortion services.
[14] At the Saskatchewan Party leadership convention, held on January 27, 2018, Cheveldayoff finished third; he was eliminated on the fourth ballot, having received 30% of votes.
[17] The 2024 general election saw Cheveldayoff win his sixth consecutive term, making him the assembly’s current longest-serving member.