The very first chuckwagon competition at the Calgary Stampede occurred in 1923. Stampede founder Guy Weadick recruited ranchers to enter their chuckwagon and roundup crews in competition, and the Rangeland Derby was born.

Billed as the No. 10 Event evening competition, the "Cowboy's Chuck-Wagon Race" offered purses and prizes totaling $275. An outfit consisted of four horses, a wagon, a driver and four helpers. The Yukon's Bill Sommers won the first race. For the Official Canadian Championship, each outfit was required to "Cut a figure eight around barrels, out through backstretch into track, run around track back to camp ground, unhook team from wagon, stretch fly. No less than two stakes, and make fire. First smoke decides winner."

First place Day Money was $25, with $15 and $10 for second and third. The entrant winning the greatest number of races out of five was awarded a special prize: a $25 John B. Stetson hat.

Over the years the sport and the format evolved. In 1975 entry became limited to the top 32 outfits from the Canadian Professional Rodeo Association. In subsequent years various independents and rodeo associations were invited to compete. Currently the Stampede invites the top 16 drivers and outfits from the previous year's GMC Rangeland Derby back, joining a selection of drivers from the two professional circuits.