The 1998 Calgary Stampeders season was the 41st season for the team in the Canadian Football League and their 64th overall. The Stampeders finished first in the West Division for the seventh time in nine seasons with a 12–6 record. The Stampeders defeated the Edmonton Eskimos in the West Final and then beat the Hamilton Tiger-Cats in the 86th Grey Cup in the first Grey Cup matchup between those two teams. Wally Buono completed his seventh season as the team's head coach and fifth as the general manager. It was the fourth Grey Cup victory in Stampeders history and Buono became the first head coach to win multiple Grey Cup championships for the franchise.