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.

League news

The Canadian Football Council (CFC) withdrew from the Canadian Rugby Union (CRU) to become a separate entity. As a separate entity, the CFC decided to rename its league the Canadian Football League (CFL) on Sunday, January 19, at the Royal Alexandra Hotel in Winnipeg. The CRU deeded the Grey Cup to the newly-minted CFL, officially locking amateur teams out of Grey Cup play. 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. The Commissioner of the CFC, Winnipeg's G. Sydney Halter, QC, was reappointed as the first-ever CFL commissioner. The CFL officially opened its operations on Thursday, August 14, as 18,206 spectators watched the Winnipeg Blue Bombers defeat the Edmonton Eskimos 29–21 at Winnipeg. 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.

Regular season

Final regular season standings

Note: GP = games played, W = wins, L = losses, T = ties, PF = points for, PA = points against, Pts = points

Grey Cup playoffs

Playoff bracket

Division Semi-Finals

Division Finals

Grey Cup Championship

CFL Leaders

1958 Eastern All-Stars

Offence

Defence

1958 Western All-Stars

Offence

Defence

1958 CFL Awards

1958 Miss Grey Cup