60 years of classics: A look back at the history of the Roughriders-Bombers rivalry on Labour Day

WATCH: Football and Labour Day go hand in hand in Saskatchewan and the rivalry the weekend hosts each year is one with deep roots in the CFL

Football and Labour Day go hand in hand in Saskatchewan and the rivalry the weekend hosts each year is one with deep roots in the Canadian Football League (CFL).

This weekend’s rendition of the Labour Day Classic between the Saskatchewan Roughriders and Winnipeg Blue Bombers will be the 60th matchup between the two clubs on the summer’s final long weekend.

“It was a part of my childhood, which was a long time ago,” Roughriders’ senior journalist and team historian Rob Vanstone told CTV News. “It feels like a Grey Cup in September.”

Vanstone has been to the last 50 Labour Day games.

He believes, of all the historic rivalries throughout the CFL, the Classic at Mosaic is the best.

“This one is really hard to top,” Vanstone said. “These are two flagship franchises and even when the teams haven’t been having great seasons, these games are more often than classics and have lived up to the label.”

All-time against Winnipeg on Labour Day, Saskatchewan is 38-21 in 59 previous matchups dating back to 1949.

There has never been a tie between the two teams.

The first of 60

To have a history as long as the Roughriders and Bombers rivalry has, there must be a memorable first.

Monday Sept. 5, 1949 – the first Labour Day matchup between Saskatchewan and Winnipeg at old Taylor Field.

“Taylor Field had just been expanded,” Saskatchewan Sports Hall of Fame’s Matthew Gourlie said. “There was a crowd of 7,500 attendance, which would be the biggest crowd ever seen [at a] football game in the province up to that point.”

1949 was also just the second season which the Roughriders wore their famed Green and White colour scheme.

“They’re wearing all white jerseys for the first time in their history,” Gourlie said. “It was also the second game of the season. Now we think of Labour Day as being the midpoint of the season at this point – it was a Rider’s home opener [in 1949].”

Vanstone says the Riders and Bombers did play a select few games prior to 1949, but the 60-year Labour Day history marks the modern, post-World War II era.

Earlier this week, the Saskatchewan Sports Hall of Fame and Provincial Archives hosted an evening discussing the history of the game – including the screening of old video of that very first Labour Day Classic, although it was not called that then.

“It doesn’t really resemble what we know [about football] today,” Vanstone said. “Touchdowns were five points. Teams would scratch and claw to get a rouge – whereas now it’s sort of a consolation prize.”

“When you look at the fans, some of them look like they’re sitting on the players bench, and the players benches were adjacent to each other,” he added.

All-time Rider greats such as Sammy Pierce and quarterback Doug Belden led the Green and White to a 20-0 win over the Blue Bombers 76 years ago.

The game also featured something Labour Day has not seen since: a dog running onto the field.

“While the Bombers were running a play, the dog almost timed the waggle perfectly for the Bombers play near their goal line,” Vanstone explained.

“Preserving history is really important and this is a fun way to show that history to people,” Gourlie added. “Hopefully it makes them think about broader history and preserve [it] for future generations.”

The next 58

Over the past 76 years since the first, Labour Day has continued to produce classic moments, career defining games, spectacular finishes and even some heartbreak.

“1951 was the first game to be called, ‘the Classic,” Vanstone said. “[Winnipeg] won 25-20, but it was just such a great game Rider fans and Bomber fans raved about it. That’s the one that lit the fuse as far as what kind of game [Labour Day] could be.”

A game stuck in Vanstone’s mind is the 1983 game. Saskatchewan won 32-30 on a 41-yard field goal from Ken Clark – just days after the death of his mother.

“I will always love that game,” Vanstone said.

Over the course of our nearly 20-minute interview with Vanstone, he rattled through the most memorable moments in Labour Day history. Some which are all-time CFL moments.

1985, Riders win 34-30 on a last-minute touchdown pass from Joe Paopao.

2002, Rocky Butler’s 165-yard, three touchdown passing game in his first professional start at quarterback.

2003, Bombers’ running back Charles Robers led the way for Winnipeg with 124 rushing yards.

2007, Kerry Joseph’s quarterback draw for a 27-yard rushing touchdown in the dying seconds of the game to give Saskatchewan a 31-26 victory – a then Grey Cup preview.

“If you did a poll, that’s the one which would win being the iconic play in this iconic game,” Vanstone said.

2015, winless Roughriders defeat Bombers for first win of the season.

2019, Brett Lauther’s walk-off field goal to win the game before he sprinted to Mosaic Stadium’s Pill Country to celebrate with fans.

2023, Regina-product Jaxon Ford tips a pass on the final play to seal a Saskatchewan win in overtime, the only Labour Day Classic game between the two teams to end in OT.

2024, Winnipeg wins 35-33 when a last-second Lauther FG attempt comes up short.

All just singular moments amongst a timeline of memorable moments making the Roughriders-Bombers’ rivalry the best in the league.

“When those teams have that staying power, this game has that staying power and these fan bases are as popular as they are, it’s become an event,” Vanstone said. “It’s a friendly rivalry. [Fans] agree to disagree on football allegiances for three hours and then the cordiality resumes.”

Labour Day without the rivalry

While the Bombers have visited Regina nearly 60 times over the past seven and a half decades, there have been a few instances where Winnipeg has not been the Riders’ opponent on Labour Day.

At times, the B.C. Lions or Montreal Allouettes would play against Saskatchewan, but the tradition of the game being at Taylor Field was still the norm.

In fact, Labour Day 1976 is one of Vanstone’s favourite CFL games ever – against the Lions.

“Riders won 17-14,” he vividly remembered. “18-yard touchdown pass from Ron Lancaster to Rhett Dawson on 3rd-and-10. That game was so good.”

With four minutes remaining in the game, Lancaster was helped off the field after taking a hard hit.

When Saskatchewan recovered a fumble, Vanstone says all eyes in Taylor Field were on the quarterback.

“Slowly he removed his cape. Slowly he walked onto the field,” Vanstone described. “Four plays, 44-yard touchdown drive, culminating with that touchdown pass to Dawson.”

However, each year since 1982, it has been the Bombers lining up against the Riders on Labour Day weekend.

2025 marks 42-straight seasons of the annual matchup, not including the pandemic-cancelled 2020 season.

“All those games were so good, they just cemented Riders versus Bombers on Labour Day weekend,” Vanstone said. “I can’t actually find any evidence of the teams saying, ‘Okay, we’re just going to play each other every year.’ It just makes so much sense.”

And while there has been a recent taste without the annual rivalry on Labour Day, Vanstone cannot envision a year without it.

“There would be no purpose served,” he joked. “And I’m sure fans would make their displeasure known.”

Remembering history

Both sides recognize the historic rivalry between Saskatchewan and Winnipeg.

“The provinces are right next to each other, the fan bases are always chirping each other about championships and records during the season and whatnot,” Riders’ quarterback Trevor Harris told media Wednesday. “I’ve heard fans say, ‘I don’t care how many games you win, just beat Winnipeg on Labor Day.”

“There’s a lot of passion there,” he added.

“The rivalry is awesome,” Bombers head coach Mike O’Shea told media Thursday. “It menas the CFL is alive and well. I certainly take it in on the way [to the stadium], and you can’t miss it when you’re heading into the city.”

“You feel the energy, which I think is excellent,” he added.

Riders head coach Corey Mace says he showed his players a video this week highlighting the game’s deep history.

“It’s out of respect for our fanbase,” he told reporters Saturday. “The fans were showing up [in 1949]. I just wanted the guys to understand how much this game means to this fanbase and ultimately, allow them to reflect and have the gratitude they get to go out there and represent this province.”

The Riders will be in their retro Green and White jerseys – as has become the tradition for the team on Labour Day weekend.

Kickoff Sunday is 5 p.m. at Mosaic Stadium.