Defending the Cup – A look back at each season the Saskatchewan Roughriders defended the Grey Cup 

Defending the Cup – A look back at each season the Saskatchewan Roughriders defended the Grey Cup 

 Written by: Tom Fuzesy

1967 

The first year the Saskatchewan Roughriders were defending Grey Cup champions was in 1967 after they had won their first Grey Cup in Vancouver 29-14 against the Ottawa Rough Riders in 1966. 

1966 Grey Cup Team Photo (Saskatchewan Sports Hall of Fame)

Hugh Campbell and Ron Lancaster after the 1966 Grey Cup. Vancouver Sun photo (Brian Kent). [PNG Merlin Archive] Photo by Brian Kent /Vancouver Sun (Retrieved from The Leader Post)

Al Benecick, shown on the right holding the Grey Cup, celebrates the first championship-game victory in Saskatchewan Roughriders history on Nov. 26, 1966 in Vancouver. Photo courtesy Ted Nenson (Retrieved from the Leader Post)

1967, the Riders were in a season long race with the Calgary Stampeders.  

The three games between these two teams were of utmost importance in deciding who was best in the west. The first two games were split, leaving the third game in Regina on October 22 as the deciding game. It was a windy day with gusts up to 65 kilometres per hour, so scoring in quarters when playing with the wind, instead of against it, was crucial. The Riders opted to take the wind in the fourth quarter with the Stampeders leading 18-11. Despite having the wind, the Riders fumbled once and threw three interceptions, nullifying their offensive output so that Calgary won 19-11.  

The Riders and Stamps finished with identical 12-4 records, with Calgary securing first place due to them winning two of three games over the Riders.  Interestingly, the year prior in 1966 the Riders finished first with three fewer wins at 9-6-1.  

The playoffs arrived and the Riders hosted Edmonton in a semi-final game on Remembrance Day, winning convincingly 21-5 on a snow-covered field. The poor field conditions restricted quarterback Ron Lancaster who only completed five receptions for 60 yards, but George Reed ran for 150 yards to aid in the Riders’ victory. 

The western final was a best of three affair with Calgary hosting games one and three and the Riders hosting game two. In game one in Calgary on Saturday, November 18, the Stampeders edged the Riders 15-11. In game two on Wednesday, November 22, the Riders eked out an 11-9 victory. A big blow to the Stampeders was losing Terry Evanshen, the top Canadian player in 1967, to a broken leg. The third and deciding game was won by the Riders 17-13 on Sunday, November 26. George Reed excelled again by rushing for 201 yards.  

Ottawa – 1967 – The 1967 Grey Cup game at Lansdowne Park. Blair Stannard (Facebook)

For the second consecutive year, the Riders were back in the Grey Cup played in Ottawa against the Hamilton Tiger Cats. At the Grey Cup award ceremony, Rider defensive tackle Ed McQuarters won lineman of the year.  

The game result wasn’t as fortunate for the Riders as in 1966 as they only mustered a single point in a 24-1 loss. It was the fifth post season game for them after playing a gruelling three games in nine days western final, so fatigue and injuries were factors. Hamilton had a much easier schedule, only playing two playoff games a week apart in the two-game total point eastern final. Another factor in the Rider loss was facing the ferocious Hamilton defence who played their sixth consecutive game not giving up a touchdown. 

Although not repeating as Grey Cup champions in 1967, the Riders could look upon the year as a success. Edging out the resurgent Calgary Stampeders for western supremacy was a significant achievement. Also winning the most games the Riders had ever won by that time at 12-4 was a huge accomplishment. This ended up beginning a very successful four-year span where the Riders won at least 12 games each year. They were 12-3-1 in 1968, 13-3 in 1969, and culminated the winning streak with their best all-time record of 14-2 in 1970. 

1990 

The Saskatchewan Roughriders were the defending Grey Cup champions in 1990 after beating the Hamilton Tiger-Cats 43-40 in Toronto in 1989 for the first championship since 1966. 

Saskatchewan Roughriders Celebrate their win in the 1989 Grey Cup (Retrieved from Sportsnet.ca)

As the 1990 season dawned, Tom Burgess, who had shared the quarterback duties with Kent Austin for the previous three seasons, left to play for Winnipeg. It was Kent Austin’s team now. 

Hopes of a Grey Cup repeat started with a Grey Cup rematch as the Riders edged the Hamilton Tiger Cats 38-35 on a back-and-forth game. The Riders needed an 86-yard late game touchdown to secure the victory. 

But the season stumbled immediately after when the Riders lost four of their next five games all against western opponents to be 2-4 after the first third of the season, putting them in last place in the western division. This slump included a 54-16 loss to the Stampeders at Taylor Field on July 27. This was the fifth worst game at that time in Rider history in terms of points allowed. 

Offensively, the team exploded in their next three games scoring at least 46 points in each game. This three game win streak culminated in a 55-11 beating of the Winnipeg Blue Bombers in the Labour Day Classic. It was the third highest points scored in a game. It was the return of Tom Burgess who didn’t have a game to remember. 

Halfway through the season they were 5-4 in third place just behind Edmonton and Calgary and five points ahead of BC. 

The second half of the season lacked any winning streak but also lacked any losing streak. Starting with the Labour Day win over Winnipeg, the Riders switched between winning and losing for the rest of the season. This winning and losing back and forth enabled the Riders to maintain a cushion over the last place BC. Lions. However, it prevented them from moving up in the standings, so they finished third with a 9-9 record. This was the identical record and position that they had in 1989.  

Whereas in 1989 the Riders had to win first in Calgary and then Edmonton to get to the Grey Cup, 1990 had them first going to Edmonton for the western semi-final.  

On a cold snowy field at Commonwealth Stadium in Edmonton, the two teams took turns taking the lead up until the third quarter. Edmonton scored the final 15 points of the game to win 43-27. The Riders were eliminated and Edmonton went on to face Calgary in the western final. 

In many respects, 1989 and 1990 were very similar for the Riders. Both years they were 9-9 and in third place. The difference was that in 1989 the Riders got hot in the playoffs and Grey Cup, and in 1989 they couldn’t get past Edmonton in the semi-final. 

2008 

 The Riders were in the rare position of needing to hire a new head coach after winning the Grey Cup 23-19 against Winnipeg the previous year in Toronto.  

Saskatchewan Roughriders centre Jeremy O’Day (54) lifts the Grey Cup among celebrating fans after his team won the CFL championship game against the Winnipeg Blue Bombers on Nov. 25, 2007 inside Toronto’s Rogers Centre. Photo by Dave Abel /Toronto Sun; Dave Abel (Retrieved from the Leader Post)

In January 2008, Kent Austin left after one year of being a Rider coach to become the offensive coordinator at the University of Mississippi. Ken Miller was selected as the new head coach, guiding the team through their Grey Cup defending year. 

As a further obstacle, quarterback Kerry Joseph who led the Riders to their Grey Cup victory in 2007 and won the CFL’s most outstanding player award that year was traded Toronto in March 2008. Taking up quarterbacking duties would be Michael Bishop, Darian Durant, Marcus Crandell, and Steven Jyles. 

The season started just where it left off when the Riders won their first six games. It was the first time since 1934 that they had won their first six games in a season. Going back to 2007, they had won their last 15 out of 16 games in the season. 

However, the Riders were running into many injuries, and it caught up to them. Despite winning back-to-back games against Winnipeg at the beginning of September, they lost five other games. Therefore, after losing 37-12 in Montreal in late September, they were 8-5 and no longer in first place behind Calgary who were 9-4. 

It was during this stretch of games that Rider Nation and the whole CFL family were saddened by news of the death of Ron Lancaster on September 18, 2008, at age 69. An iconic quarterback of the Roughriders from 1963 to 1978, Lancaster also held coaching stints in Saskatchewan, Edmonton, and Hamilton.  

As October approached, an upcoming back-to-back series with Calgary was critical to the Riders’ first place hopes. They won the first game, edging out the Stampeders 37-34 in Regina. However, the second game in Calgary the wheels came off, and the Riders lost 42-5, giving the Stamps a two-point cushion in the standings plus the tiebreaker.  

Despite winning the remaining three games and ending up 12-6 matching their record in 2007, they couldn’t catch Calgary at 13-5. A home semi-final game against BC was on the schedule. 

The game was disappointing as the Riders did not play well. The biggest issue was the Riders committed seven turnovers, including four in the first quarter, giving BC control of the game early that they never relinquished. The Lions won handily 33-12. 

Overall, it was similar season to 2007 in that the Riders finished 12-6 in second place. The difference was the lack of playoff success in 2008 when the Riders’ quest of being Grey Cup repeat champions came to quick end. 

2014 

 The Roughriders defeated the Hamilton Tiger Cats 45-23 to win the 2013 Grey Cup in Regina.

The team started 2014 with Darian Durant entrenched as starting quarterback. The Riders started on the right foot, soundly defeating Hamilton 31-10 to kick off the season with a Grey Cup rematch.  

Two subsequent losses followed, including a 48-14 beating in Toronto that raised some eyebrows as to the potential of a Grey Cup repeat. 

However, seven straight victories put the Riders at 8-2 and within a game of the 9-1 Stampeders.  

Despite winning their seventh straight game in Winnipeg on September 7, celebration was diminished when Darian Durant suffered a season-ending injury when he tore a tendon in his right elbow. It was Tino Sunseri and Seth Doege who replaced him as quarterback. The Riders also brought back 41-year-old Kerry Joseph in October. 

CFL action in Regina on Saturday July 12, 2014. (CFL PHOTO – Derek Mortensen)

The Riders’ fortunes soured quickly after Durant’s injury. They lost 28-3 against the 2-7 Tiger Cats in Hamilton. After edging out Ottawa 35-32, they lost five in a row including 24-0 in Edmonton and 40-9 in Montreal. 

They won their last game against Edmonton, finishing the season in third place at 10-8. The semi-final game was set to go in Edmonton. 

 It was not to be for the Riders as Kerry Joseph threw five interceptions setting a CFL playoff record as Edmonton jumped to a 17-0 lead. That was all they needed as they won 18-10, eliminating the Riders and their aspirations for a Grey Cup repeat. 

The 2014 season can be summarized by basically one thing: Darian Durant’s injury and the Riders left scrambling for a suitable replacement. Who knows what would have happened if the injury hadn’t occured? At 8-2, the Riders had a chance for first place and perhaps another Grey Cup trip. But it was never to be. 

2026

As the 2026 season starts, thoughts of a repeat Grey Cup championship are on the minds of many Rider fans.

Saskatchewan Roughriders quarterback Trevor Harris hoists the Grey Cup.TSN screenshot

Repeat champions in the CFL have actually been quite rare in recent history. Since 1982, when Edmonton won their fifth Grey Cup in a row, there have been 42 Grey Cup champions, but only three of them were repeats. Gone are the days when long-term dynasty teams were more common. The frequent Winnipeg/Hamilton Grey Cups in the late 1950s and early 1960s, and the Edmonton/Montreal matchups in the mid-1950s and 1970s, showcased the clear dominance of those teams.

The Riders themselves have failed to repeat as champions following any of their four previous Grey Cup victories. Once, in 1967, they made it back to the big game but lost. The other three times—in 1990, 2008, and 2014—they fell in the Western Semi-Final.

Early predictions put the Riders near the top, if not at the very top, of the power rankings. However, it’s a common belief that repeating as champions is harder than winning the first time around. Football is an unpredictable sport with countless variables and intangibles. Will injuries derail the season? Will quarterback Trevor Harris continue to be effective? Will depth in certain position groups become a problem? Will a “Grey Cup hangover” play a role, where the hunger for a repeat isn’t quite as fierce as the desire for that initial championship? Will opposing teams play with an extra spark just for the chance to unseat the reigning champs?

There are plenty of questions to be answered. There’s no need to make any bold predictions just yet, other than to say the Riders likely have as good a shot at hoisting the trophy as anyone else.

What will happen? Who knows? We’ll soon find out…