The 1958 CFL season was the inaugural season of the Canadian Football League, although the season structure was essentially unchanged from the one established three years earlier when the league's founding unions (the Interprovincial Rugby Football Union and the Western Interprovincial Football Union) had effectively barred amateur teams from competing for the Grey Cup.
The Hamilton Tiger-Cats and Winnipeg Blue Bombers met again for Canadian football supremacy.
The Blue Bombers turned the tables on the Tiger-Cats this time, winning their first Grey Cup since 1941.
However, the Grey Cup had been the de facto professional football championship of Canada since the Ontario Rugby Football Union withdrew from Grey Cup competition in 1954.
A regular season game was played in the United States, at Philadelphia's Municipal Stadium on September 14 as the Hamilton Tiger-Cats defeated the Ottawa Rough Riders by a score of 24–18.