On May 20, 2018 Cheveldayoff was caught trying to sell tickets outside a Winnipeg Jets NHL hockey game after being stood up by his buddy and his buddy’s mom.

On August 28, 2017, Cheveldayoff announced his bid for the leadership of the Saskatchewan Party just days after party leader and Premier Brad Wall announced that he was retiring from politics. The Saskatchewan Party leadership vote, held on January 27, 2018, was won by Scott Moe. Moe was sworn in as the 15th Premier of Saskatchewan six days later, on February 2.

With the Cabinet shuffle on August 23, 2016, Cheveldayoff was asked by the Premier to serve as Minister of Parks, Culture, Sport and Minister responsible for the Public Service Commission (PSC).

In 2014, Cheveldayoff was appointed Government House Leader.

First elected in November 2003, Cheveldayoff was the Opposition Critic for Finance, Deputy Critic for Learning (Post-Secondary Education), and was a member of the Public Accounts Committee. He also served as Deputy Chair of the Standing Committee on Human Services. After being re-elected in 2007 as a member of the government, he was appointed to cabinet as the Minister of Crown Corporations. In a cabinet shuffle in 2009, he became Minister of Enterprise, and in 2010, he was appointed Minister of First Nations and Métis relations. On May 25, 2012, Cheveldayoff was appointed Minister of Environment, Responsible for SaskWater and the Water Security Agency.

Cheveldayoff ran in the 1993 Canadian federal election for the Progressive Conservative Party in the riding of The Battlefords—Meadow Lake. At the time the seat was held by Len Taylor of the New Democratic Party. Cheveldayoff finished a distant fourth.

Cheveldayoff holds a B.A. (Honours) in Economics and Political Science (1988) and a Masters of Business Administration (1996). He was a parliamentary page in the House of Commons and won the Queen Elizabeth II scholarship for excellence in Parliamentary Studies.

Ken Cheveldayoff (born April 1, 1965) is a Canadian provincial politician. He is the Saskatchewan Party member of the Legislative Assembly of Saskatchewan for the constituency of Saskatoon Willowgrove. In 2018 he was a candidate for the leadership of the Saskatchewan Party.