Prior to 2004, the club operated as a corporation without share capital (no person or entity "owned" the team or any portion of it), an ownership structure the Blue Bombers have used continuously.

The club was given a bye and advanced straight to the Grey Cup finals for the first time, but were severely outmatched, losing 54–0 to Queen's University at Varsity Stadium in Toronto.

[17] This was, and still is, the most lopsided defeat in Grey Cup history as the defending champion Queen's won their third straight national championship at the expense of the Regina Rugby Club.

The origin of the name has multiple theories, the most credible of which describes how the North-West Mounted Police were called Roughriders because they broke the wild horse broncos that were used by the force and the moniker was adopted from them.

However, due to a rules dispute with the Canadian Rugby Union over use of their five import players from the United States, Regina was barred from competing for the 24th Grey Cup.

While visiting a surplus store in Chicago, executive member Jack Fyfe found a set of green and white uniforms and purchased them for the Roughriders.

Following their 1956 campaign, tragedy struck the Roughriders franchise when four members of the team were killed in a plane crash on December 9, 1956, while returning from the Canadian Football Council (CFC) All Star Game in Vancouver.

Gordon Sturtridge, Mel Becket, Ray Syrnyk, and Mario DeMarco were killed when Flight 810 crashed into Slesse Mountain near Chilliwack, British Columbia.

In 1965 after one year as the offensive coordinator, Eagle Keys became the head coach of the Roughriders and guided them to an 8–7–1 record and an appearance in the western semi final which they lost to the Winnipeg Blue Bombers 15–9.

Ron Lancaster won the Jeff Nicklin Memorial Trophy as the Western Conference's most outstanding player while George Reed, receiver Hugh Campbell and four other Riders were named league all-stars, the most from any team that year.

[40] The 1968 season saw the Roughriders finish with the best record in the league at 12–3–1, although they placed 1st in the west division they lost the western final series to the Calgary Stampeders 2–0 by a combined score of 57–12.

[41] Dave Skrien was hired as the next head coach of the Roughriders and led them as they continued their winning ways, namely with an appearance in the 1972 Grey Cup, which yielded another Saskatchewan loss to Hamilton.

The Riders then had three consecutive second-place finishes and West Final losses to the Edmonton Eskimos, ending when George Reed retired after the 1975 season as the all-time leading rusher in all of professional football with 16,116 rushing yards.

In 1976, the Roughriders recaptured first place in the Western Conference and defeated the Eskimos in the West Final, advancing to the Grey Cup to once again play the Ottawa Rough Riders.

The Roughriders had several talented players during this era, including Joey Walters at receiver, Vince Goldsmith at defensive end, offensive lineman Roger Aldag from Gull Lake and Dave Ridgway, who became one of the greatest kickers in CFL history.

Roughriders management subsequently explained that loan, equal to roughly C$4 million or $500,000 for each of the then-eight CFL teams at contemporary exchange rates, had been agreed between the leagues in principle but not finalized in time for the telethon, and thus had to remain confidential until formally announced by the respective commissioners.

The 2003 season saw the Roughriders earn their first winning record since 1994, finishing 11–7 and in third place, building optimism in a year where the franchise was hosting their second ever Grey Cup game.

Saskatchewan placekicker Paul McCallum missed an 18-yard field goal while BC kicker Duncan O'Mahoney hit a 40-yarder to win the game for the Lions, adding to the frustration of the Roughrider fanbase.

After contending on and off in the early part of the 21st century, the Roughriders hired 1989 Grey Cup hero Kent Austin as head coach and Ken Miller as offensive coordinator in the 2007 season.

The following offseason was a difficult one for the Roughriders, as they lost top players Kory Sheets and Weston Dressler to the NFL and key leaders Mike McCullough, Renauld Williams and Geroy Simon to retirement.

2014 training camp found starters in Anthony Allen and Brett Swain as the Roughriders went out to attempt the first repeat championship season in franchise history.

Joseph, alongside new running back Jerome Messam and receiver Korey Williams won one game before losing to the Edmonton Eskimos in the Western Semi Final.

To begin the year, the Roughriders found a linebacker, Jeff Knox Jr, in training camp and he became an immediate starter next to Shea Emry and Weldon Brown.

During the August 30, 2015 game against the Ottawa Redblacks, head coach Corey Chamblin made the decision to bench Smith in favour of Tino Sunseri following an interception, which disgusted many Roughrider fans.

Following another disappointing loss to Ottawa and a record of 0–9 for the first half of the season, head coach Corey Chamblin and general manager Brendan Taman were fired on September 1, 2015.

This, combined with the team's share of revenues from the 2022 Grey Cup (held at Mosaic Stadium as a replacement for the cancelled 2020 championship game) allowed the club to replenish its stabilization fund back to pre-pandemic levels.

They were known for their strict allegiance to the Riders,[citation needed] standing through the entire game, and often being merciless to opposing fans who sit in the section and cheer for the road team.

system plays the cult hit "The Last Saskatchewan Pirate" by The Arrogant Worms, and the Riders Cheer Team leads the crowd in a fourth quarter stretch.

[93][94] For the 2022 season, Michael "Ballsy" Ball—who hosted CKRM's pre-game and post-game shows, was play-by-play announcer for the Regina Rams, and co-hosted sister station CFWF-FM's morning show—became the new voice of the Roughriders.

[95][94] In 2024, he was replaced by Dave Thomas, a former broadcaster for the Saskatoon Blades (CJWW) and Weyburn Red Wings (CFSL), and previously a pre-game host and sideline reporter for the Riders.