It was a taste of success to come that decade under the direction of head coach Les Lear and talented stars such as Woody Strode, Paul Rowe, Keith Spaith, Dave Berry, Normie Kwong and Ezzert "Sugarfoot" Anderson.

The year 1948 was perhaps the greatest season in Stamps history, achieving a perfect regular season of 12–0 and capping the year a 2-0-1 record in the playoffs including a Grey Cup victory over the Ottawa Rough Riders at Toronto's Varsity Stadium, memorable for the team's scoring a touchdown on a "sleeper play".

It was also during that same Grey Cup festival that Calgary fans brought pageantry to the game and made it into a national celebration, featuring pancake breakfasts on the steps of City Hall, starting the Grey Cup parade and even riding a horse in the lobby of the Royal York Hotel.

It was 19 years until Calgary once again reached the Grey Cup, losing 24–21 to Ottawa in the 1968 final and not until 1971 when they were crowned champions, defeating the Toronto Argonauts 14–11.

After having some great years at the end of the 1960s which culminated in their 1971 Grey Cup championship, 1972 started a long period of struggles for the Stampeders.

However, a successful Save Our Stamps campaign in 1986 resulted in season ticket sales of 22,400, additional funds and stability that translated to improved on-field play which laid the groundwork for both their first playoff win since 1979 in 1990, and back-to-back Grey Cup berths in 1991 and 1992 when they won the title over Winnipeg.

Led by quarterbacks Doug Flutie, Jeff Garcia and Dave Dickenson, receivers Allen Pitts, Terry Vaughn and Dave Sapunjis, and a rock-steady defence led by Western All Stars Alondra Johnson, Stu Laird, and Will Johnson the Stampeders racked up a 153–79–2 record during these years.

In 1996, Ryckman was found by the Alberta Securities Commission to have run a stock manipulation scheme, was fined $492,000 and was forced to give up the Stampeders, who were subsequently purchased by Sig Gutsche via a receivership court for $1.6 million on April 3.

[13] In 2008, one-time Stamps QB John Hufnagel took the coaching reins, and the Stampeders ended their playoff victory drought en route to winning the team's sixth Grey Cup 22–14 against the Montreal Alouettes.

The Stamps continued their success in 2016, winning the West Division again with a 15–2–1 record, but falling to the third-year Ottawa Redblacks in the 104th Grey Cup in overtime.

In 2017, the Stampeders finished 13-4-1 (with the league's best record for the season) and made their second straight Grey Cup appearance, but lost to the Toronto Argonauts again, just as they did five years earlier.

The CFL went on hiatus in 2020, but returned in 2021, and the Stampeders finished one game back of the Saskatchewan Roughriders in the shortened 2021 season with an 8–6 record.

On December 12, 2022, it was announced that Dickenson had been named the team's new general manager in addition to retaining his head coaching duties.

[18] As of 2012[update], 29 players have won the award, including three-time winners Henry Burris, Danny Barrett and Stu Laird.