In its early years, the Cowboys were part of the Oklahoma Intercollegiate Conference and gradually began to build a competitive reputation. The program saw significant growth in the 1920s and 1930s, with the construction of Lewis Field in 1920, which provided a home for the team and a venue for thousands of fans to rally behind their players. The team adopted its iconic orange and black colors, which have since become synonymous with Oklahoma State athletics.

The turning point for the Cowboys came in the 1940s under head coach Jim Lookabaugh, who led the team to its first conference championships. The success helped solidify Oklahoma State’s position in college football, and the team began to attract more attention both regionally and nationally.

In 1958, the program achieved a significant milestone by joining the Big Eight Conference, which further elevated its competitiveness. This period saw the emergence of notable players and coaches, including legendary coach Jimmy Johnson in the 1980s, who would later gain fame in the NFL. Under Johnson's leadership, the Cowboys achieved a national ranking and were invited to bowl games, enhancing the program's prestige.

The 1990s and early 2000s were marked by ups and downs, but the hiring of head coach Mike Gundy in 2005 ushered in a new era of success. Gundy revitalized the program, leading the Cowboys to multiple bowl appearances and significant victories over traditional rivals. The team's performance soared, highlighted by a Big 12 Championship in 2011 and consistent rankings in national polls.

Oklahoma State football is not just known for its competitive spirit; it also boasts a passionate fan base and a unique game-day atmosphere at Boone Pickens Stadium. The integration of tradition, community involvement, and academic commitment has solidified the Cowboys' identity both on and off the field.

Today, the Oklahoma State Cowboys football program continues to be a vital part of the university’s athletic landscape, contributing to the legacy of college football in the United States. With a commitment to excellence, the Cowboys aim to build on their storied past while aspiring for future successes in the ever-evolving world of college athletics.