Missing rings: the five best teams that didn’t win the Grey Cup in the last 35 seasons

Photo: Arthur Ward/3DownNation. All rights reserved.

Sometimes in sports, the best team doesn’t win the championship.

In fact, of the record-holders for regular-season wins in the five major North American sports — NFL, CFL, NHL, NBA, MLB — none won the championship in the years they set the record.

The 2016 Golden State Warriors lost the NBA title to LeBron James and the Cleveland Cavaliers. The 16-0 New England Patriots from 2007 shockingly lost the Super Bowl to a 10-6 New York Giants team. The 1906 Chicago Cubs and 2001 Seattle Mariners both failed to win the World Series those years, and the 1995-1996 Detroit Red Wings won 62 games but lost in six games to the Colorado Avalanche in the Western Conference Finals.

The CFL is no stranger to those types of upsets. Since the implementation of the 18-game schedule in 1986, we have seen some record-setting teams fly through the regular season only to be smacked in the mouth before attaining their ultimate goal. We saw it this past season when the 15-3 Winnipeg Blue Bombers failed in their attempt at a three-peat and fell to the 11-7 Toronto Argonauts in the 109th Grey Cup.

The 2022 Bombers do not make this list, not only because I did not want to become a prisoner of the moment but also because the majority of that team has two other Grey Cup rings with which to console themselves.

The other teams on this list are not so lucky, so here are what I believe to be the five best single-season teams to not win the Grey Cup in the last 35 years.

Photo courtesy: Scott Grant/CFLPhotoArchive.com

5. 1989 Edmonton Football Team
Result: Lost West Final to Saskatchewan, 32-21

Remember that point about the teams with the most regular-season wins in league history not winning a championship? In the CFL, that team is the 1989 Edmonton Football Team.

The green and gold were a juggernaut in the final year of the 1980s, winning a record 16 games and setting a then-record of 644 points scored while also having an astounding plus-342 point differential. There is an argument to be made that this is the most dominant team in CFL history, except for one small problem: they did not even make the Grey Cup.

Now, this franchise and a lot of the players from this team won a championship in 1987 and/or 1993, but the 1989 team not winning it all robbed them of something even bigger than a championship: immortality.

Had this 16-win team won the Grey Cup, they might be known as the greatest CFL team of all time. I know there have been other great CFL teams, especially in Edmonton, but a regular-season record for wins in the dominating fashion with which they accumulated them, coupled with winning the championship would put this team in rarified air.

If I believe a championship could have pushed them into greatest-of-all-time territory why do they only rank fifth? Simple. They failed to win a single playoff game.

Instead of setting up a matchup with the 12-6 Hamilton Tiger-Cats in Toronto that year, Edmonton fell on home soil to a 9-9 Saskatchewan Roughriders team that allowed more points than they scored in 1989.

The Riders were one of just two teams to beat Edmonton in the regular season that year, notching a 48-35 victory in Regina in mid-September, but the other two games between the two teams were not particularly close. Edmonton won 45-19 and 49-17, their last victory coming in the final game of the season. That didn’t matter once the playoffs rolled around.

Photo Scott Grant / CFLPhotoArchive.com
Photo courtesy: Scott Grant/CFLPhotoArchive.com

4. 2019 Hamilton Tiger-Cats
Results: Lost Grey Cup to Winnipeg, 33-12

The 2019 squad was easily the most dominant Ticats team I have ever seen and it is not particularly close. The Tabbies were in a class of their own that season, winning 15 games, scoring the most points, and allowing the fewest. Their three regular-season losses came by a combined 13 points and they did all that despite losing their starting quarterback, Jeremiah Masoli, in Week 7.

However, many seemed hesitant to believe in the team, especially early on. The history — especially recent history — showed a franchise that was not particularly trustworthy. Before 2019, the Ticats had not won more than 10 games since 2001.

By the end of the season, everyone believed in the black and gold. They had the league’s top player in Brandon Banks, the top coach in Orlondo Steinauer and a plethora of division and league all-stars. The Ticats easily dispatched an overmatched Edmonton squad in the East Final to set up a date with destiny.

Unfortunately for those partial to the team from the steel city, victory was not theirs to be had. The Ticats ran into a blue and gold buzzsaw and instead of Hamilton fans rejoicing for the first time this century, it was their Winnipeg counterparts who felt the joy of a long championship drought ending.

Photo courtesy: Scott Grant/CFLPhotoArchive.com

3. 2001 Winnipeg Blue Bombers
Results: Lost Grey Cup to Calgary, 27-19

I don’t know if it can be overstated just how good this Winnipeg team was. Much like the 2019 Ticats, this was the Bombers team that most deserved to end their Grey Cup drought. They were a juggernaut. They were the only team to score more than 500 points and allow fewer than 400, they won 14 games, and had eight league all-stars and nine division all-stars.

The Bombers won five league awards, including Most Outstanding Player for Khari Jones, top Canadian for Doug Brown, top lineman for Dave Mudge, top special teamer for Charles Roberts and coach of the year for Dave Ritchie. Oh, and they also had this guy you may have heard of named Milt Stegall, who would set the single-season touchdown record the following year en route to becoming the first receiver to win Most Outstanding Player since 1988.

This Bombers team was loaded and, after cruising to a two-score win over Hamilton in the East Final, just needed to beat a bad Calgary Stampeders team to win their first Grey Cup since 1990. Instead, the Bombers were stunned by the 8-10, Marcus Crandell-led Stamps, losing 27-19.

Bombers fans would have to wait another 18 years before seeing their team finally reach the top of the mountain. I am sure if you asked anyone from Winnipeg which loss during their 29-year title-less streak they would like to have back, almost all of them would say this one.

Photo Scott Grant / CFLPhotoArchive.com
Photo courtesy: Scott Grant/CFLPhotoArchive.com

2. 2016 Calgary Stampeders
Result: Lost Grey Cup to Ottawa, 39-33 (OT)

Some believe the 2016 Calgary Stampeders are the greatest team in CFL history, Grey Cup loss be damned. It is an easy argument to make, too. This Stamps team was just that good.

After starting the season 1-1-1 the Stamps wouldn’t lose again until the final week of the regular season. They won 14 straight games and topped the 30-point mark in 12 of them. They owned the league and with the chance to become just the second 16-win team in CFL history, opted for rest in the final game and finished the season 15-2-1.

Opting out of history did not slow the Stamps down in any measurable way as they picked their momentum right back up and slaughtered the B.C. Lions in the West Final. The Grey Cup matchup against the 8-9-1 Redblacks felt like it would be a coronation instead of a game. There was no chance Calgary would lose.

Except they did.

The Stamps were forced to climb out of a large deficit for the first time all season before some questionable play calling in the late stages of the game by first-year head coach Dave Dickenson, as well as a great defensive play by Redblacks’ defensive back Abdul Kanneh, forced the game into overtime. That’s when the third-year Redblacks would shock everyone and pull out the improbable win.

Instead of the Stamps being hailed as one of the greatest teams of all time, Calgary was left wondering what the heck just happened as they saw the confetti fall on the first Ottawa team to win a championship in 40 years.

Two years later, with a lot of the same cast, the Stamps would get their revenge on the Redblacks, but that 2018 team was nowhere near as good as their 2016 counterpart.

Photo courtesy: Scott Grant/CFLPhotoArchive.com

1. 1994 Calgary Stampeders
Result: Lost West Final to B.C., 37-36

The Doug Flutie era of the CFL was something we may never see again.

I know that might sound obvious but Flutie’s run from 1992 to 1997 playing for both the Stamps and Toronto Argonauts was as dominant as we have ever seen from an individual player, maybe in any sport ever. Five Most Outstanding Player awards, four Grey Cup appearances, and three Grey Cup victories with his teams going a combined 88-20 to produce five straight 15-win seasons. There is a reason he is widely viewed as the greatest player in league history with an output that will never be matched.

Despite his brilliance over that span, Flutie didn’t win every Grey Cup. While a case can be made for the 1993 squad that lost to Edmonton in the West Final as Flutie’s best non-championship team, I believe the 1994 team is his best not to win it all.

Calgary scored an absurd 698 points (38.7/per game) while allowing just 355. The quick math on that shows you that Calgary’s average margin of victory was 19 points. That is damn near three touchdowns. They scored 40 or more points eight times, hung 50 burgers on Winnipeg, Saskatchewan, Toronto and Shreveport, and put 62 up on B.C.

This felt like a team that at the very least would get to the Grey Cup but after trouncing the Riders by 33 in the West Semi-Final — this came during the CFL’s ill-fated U.S. expansion era where eight teams made the playoffs and no team received a bye — the Stamps would fall in a thriller, 37-36 to the same Lions they once hung 62 on that year.

Maybe if the league only had eight or nine teams and the first-place squad received a bye into the divisional final, the 1994 Stampeders would have made it to and won the Grey Cup. Unfortunately, we will never know.

Instead, despite strong pushes from the 2016 Stamps and 2001 Bombers, the 1994 Stamps get the title of best CFL team to not win a championship.

Josh Smith has been writing about the Ticats and the CFL since 2010 and was sporting his beard way before it was cool. Will be long after, too.