Sports have a distinctive way of uniting and dividing us (in good fun). From opinions on whether a hockey player is worth the hype to debates on who the GOAT of a particular sport is, fans are geared up to join in a heated discussion any time, any place. In Canada, there’s one league that tends to be the subject of passionate debate, and that’s the CFL. With slightly adjusted rules compared to American football and its distinct Canadian identity, it’s almost considered a unique sport of its own. But one thing’s for certain—the league is full of deep history, distinguished dynasties, and binge-worthy battles that ultimately lead to the big prize: the Grey Cup.
While we could argue forever about coaching decisions and roster talent, one of the clearest measures of greatness at the end of the day is the number of Grey Cup wins a team has. Let’s take a look at the list.
Toronto Argonauts
Which team has lifted the trophy more than any other? The pride and joy of the CFL, the Toronto Argonauts. Based and named after the biggest city in the country, the Argos (as they’re affectionately called) have made a total of 25 appearances in the finals, with 19 wins and just 6 losses. The team is the most recent winner (in 2024) of the cup as of the time of writing.
The Argos have consistently proven themselves over the years, building a strong foundation with six titles in just over two decades, winning five Grey Cups in eight years, and boasting a three-peat from 1945–1947. In the ‘80s and ‘90s, the Argos kept their momentum, with notable players like Pinball Clemons and Damon Allen bringing more eyes to the sport. With no Grey Cup losses in the 21st century, the Argonauts have been a fan favourite to bet on, especially on platforms that offer a wider range of gambling options—including Apple Pay casinos on Bonus.ca—due to the convenience of having sports betting and online casino games in one place.
Edmonton Elks
Formerly the Edmonton Eskimos, the Elks come in second place with a total of 23 Grey Cup appearances, 14 wins, and 9 losses. They last won the cup in 2015, which means they have yet to win the championship under their new name. In the 2015 season, they finished the season with their best record since 1989, which was a true omen of what was to come. Similar to Toronto, the Elks had a period of dominance, winning five Grey Cups in seven years. Yet what sets them apart is their dominance in the regular season and their notably lengthy playoff streak at 34 seasons, holding the CFL record.
The secret behind these incredible achievements? A lineup of iconic players, some of whom have been inducted into the Hall of Fame. Star quarterback Warren Moon led the team to five of their appearances and four victories, while running back Mike Pringle became the CFL’s all-time rushing leader. The team has also been credited for their gritty, raw style of play, which has made them one to watch out for.
Winnipeg Blue Bombers
As the Blue Bombers are based in Winnipeg, the culture surrounding the team is certainly special. With a blue-collar mentality and a working-class spirit, they pride themselves on aligning with the resilience and grit of their community. The Blue Bombers are operated by the Winnipeg Football Club, which is a not-for-profit community organization.
While Winnipeg has made the most appearances in the Grey Cup, it has unfortunately accumulated more losses (17) than wins (12). They’re one of the five teams in the CFL with a losing record in the championship. As all sports fans know, though, the hard-earned wins often overshadow the heartbreaking losses, and so have their standout championship years and recent successes in the 2010s and 2020s. The Blue Bombers won the 2019 Grey Cup, which ended the 29-year championship drought, and then again in 2021, indicating that they’re real contenders in the CFL. Some of the team’s most notable players are not from past dynasties but from the current era, such as linebacker Adam Bighill, defensive end Willie Jefferson, and quarterback Zach Collaros.
Ottawa Redblacks
The Ottawa Redblacks were re-established in 2014, following the folding of the Ottawa Rough Riders after 120 years of play. While the Rough Riders were one of the oldest professional sports teams on the continent and won the Grey Cup nine times, they experienced struggles on the field, financially, and with ownership and attendance, creating the perfect cocktail for disaster. On top of that, their name was confused with the Saskatchewan Roughriders, making life difficult for commentators.
A few years after the Rough Riders became defunct, another attempt to establish a CFL team in the city was made—the Ottawa Renegades. They failed to succeed, and there wasn’t a team for eight years until the Ottawa Redblacks. Although the Ottawa Redblacks have only been around since 2014, they won the 2016 Grey Cup, helping end a 40-year Grey Cup championship drought for the city. Since it’s not exactly fair to compare the Redblacks’ short history to the robust legacies of teams like the Elks or Argos, we’re lumping in the records of the original Rough Riders and the Renegades.
The efforts and achievements of the previous teams weren’t for nothing, considering their unforgettable moments, Hall of Famers like Bill Symons and Russ Jackson, and their contributions to shaping the CFL.
