Tiger-Cats head coach Jim Trimble stated before the game his team would "waffle" the Blue Bombers.
Hamilton started well, opening a 14-0 lead in the first quarter. Winnipeg had got within one point when the Hamilton coach made a controversial call.
Instead of downing the ball before half time, coach Trimble elected to punt the ball away on the last play. The punt was blocked, and recovered in the end zone by Bomber Norm Rauhaus to give them a 20-14 half-time lead. "We should have won the 1958 Grey Cup but there was a bad coaching error before halftime" said Hamilton defensive lineman Angelo Mosca.
In the second half, Hamilton came back to tie, but a Hamilton fumble was recovered by Bomber Gord Rowland which led to a touchdown by Winnipeg fullback Charlie Shepard. Hamilton again fought back to take the lead 28-27. Winnipeg quarterback Jim Van Pelt scored on a trick play where he pitched the ball to running back Leo Lewis who passed back to Van Pelt for the touchdown. A Sheppard punt single closed out the scoring.
Winnipeg racked up 187 passing yards and 247 rushing yards from Shepard, Kenny Ploen, Lewis and Van Pelt. Van Pelt scored two touchdowns, four converts and two field goals, a total of 22 points.
Winnipeg hadn't won the Grey Cup in eighteen years.
The 1958 Grey Cup game is considered to be one of the ten best Grey Cup games of all time.