The 1958 CFL season was the fifth season in modern Canadian professional football, although officially it would become known as the inaugural season of the Canadian Football League (see below).
CFL news in 1958 
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 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 in pre-season action 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
- Bold text means a team clinched a playoff berth.
- Winnipeg and Hamilton both received first-round byes.
Grey Cup playoffs 
Note: All dates in 1958
- Edmonton won the total-point series by 58–12. The Eskimos went on to play the Winnipeg Blue Bombers in the Western Final.
- The Rough Riders went on to play the Hamilton Tiger-Cats in the Eastern Final.
- Winnipeg won the best-of-three series 2–1. The Blue Bombers advanced to the Grey Cup game.
- Hamilton won the total-point series 54–14. The Tiger-Cats advanced to the Grey Cup game.
Playoff bracket 
Grey Cup Championship 
- Note: Western Semi-Final dates are not confirmed; however, since (1) the regular season ended on November 1 in the West and on November 8 in the East, and (2) all other playoff dates are accurate, including the date of the Grey Cup game, it is reasonable to assume the above dates are correct.
CFL Leaders 
1958 Eastern All-Stars 
- QB – Bernie Faloney, Hamilton Tiger-Cats
- RB – Joel Wells, Montreal Alouettes
- RB – Gerry McDougall, Hamilton Tiger-Cats
- RB – Dick Shatto, Toronto Argonauts
- E – Red O'Quinn, Montreal Alouettes
- E – Paul Dekker, Hamilton Tiger-Cats
- FW – Ron Howell, Hamilton Tiger-Cats
- C – Tommy Hugo, Montreal Alouettes
- C – Norm Stoneburgh, Toronto Argonauts
- OG – Hardiman Cureton, Ottawa Rough Riders
- OG – Jackie Simpson, Montreal Alouettes
- OT – Dick Fouts, Toronto Argonauts
- OT – John Barrow, Hamilton Tiger-Cats
- DT – Milt Graham, Ottawa Rough Riders
- DT – John Barrow, Hamilton Tiger-Cats
- DE – Pete Neumann, Hamilton Tiger-Cats
- DE – Doug McNichol, Montreal Alouettes
- DG – Vince Scott, Hamilton Tiger-Cats
- DG – Jackie Simpson, Montreal Alouettes
- LB – Tommy Hugo, Montreal Alouettes
- LB – Tony Curcillo, Hamilton Tiger-Cats
- DB – Hal Patterson, Montreal Alouettes
- DB – Ralph Goldston, Hamilton Tiger-Cats
- DB – Ed Macon, Hamilton Tiger-Cats
- S – Bobby Simpson, Ottawa Rough Riders
1958 Western All-Stars 
- QB – Jackie Parker, Edmonton Eskimos
- RB – Cookie Gilchrist, Saskatchewan Roughriders
- RB – Jack Hill, Saskatchewan Roughriders
- RB – Leo Lewis, Winnipeg Blue Bombers
- RB – Johnny Bright, Edmonton Eskimos
- E – Ken Carpenter, Saskatchewan Roughriders
- E – Ernie Warlick, Calgary Stampeders
- C – Jim Furey, Calgary Stampeders
- OG – Harry Langford, Calgary Stampeders
- OG – Tom Hinton, British Columbia Lions
- OT – Don Luzzi, Calgary Stampeders
- OT – Roger Nelson, Edmonton Eskimos
- DT – Don Luzzi, Calgary Stampeders
- DT – Buddy Tinsley, Winnipeg Blue Bombers
- DE – Art Walker, Edmonton Eskimos
- DE – Herb Gray, Winnipeg Blue Bombers
- MG – Steve Patrick, Winnipeg Blue Bombers
- LB – Rollie Miles, Edmonton Eskimos
- LB – Gord Rowland, Winnipeg Blue Bombers
- LB – David Burkholder, Winnipeg Blue Bombers
- LB – Ted Tully, Edmonton Eskimos
- DB – Jack Gotta, Calgary Stampeders
- DB – Larry Isbell, Saskatchewan Roughriders
- S – Oscar Kruger, Edmonton Eskimos
1958 CFL Awards 
1958 Miss Grey Cup 
- Miss Montreal Alouettes Joan Van Boven was named Miss Grey Cup 1958