Each season, teams receive Grey Cup betting odds, and while some live up to them, others will fall short and continue to do so for years to come.
Below, I’ll examine the longest active and all-time droughts for not only Grey Cup wins, but playoff appearances in the CFL.
Last Time Every Team Won the Grey Cup
| Team | Last Grey Cup Win |
| Hamilton Tiger-Cats | 1999 |
| BC Lions | 2011 |
| Edmonton Elks | 2015 |
| Ottawa Redblacks | 2016 |
| Calgary Stampeders | 2018 |
| Winnipeg Blue Bombers | 2021 |
| Montreal Alouettes | 2023 |
| Toronto Argonauts | 2024 |
| Saskatchewan Roughriders | 2025 |
What’s the Longest Active Grey Cup Drought?
The longest active Grey Cup drought belongs to the Hamilton Tiger-Cats.
They haven’t won the Grey Cup this century, last winning it in 1999.
What’s the Longest Grey Cup Drought in League History?
The longest Grey Cup drought in CFL history belongs to Ottawa, an organization that went 40 years without winning a Grey Cup from 1976 to 2016.
What’s the Longest Active CFL Playoff Drought?
The longest active CFL playoff drought belongs to the Edmonton Elks. They haven’t made it over the last five seasons.
What’s The Longest Playoff Drought in Canadian Football League History?
The longest playoff drought in CFL history is the Saskatchewan Roughriders‘ 11-year drought.
They didn’t make the playoffs from 1977 to 1987.
The content provided in this blog is intended for entertainment purposes only. All views and opinions expressed are the authors and reflect their individual perspectives on sports, betting, and related topics. This content should not be considered professional betting advice or the official views of BetMGM LLC. Please gamble responsibly. If you or someone you know is experiencing issues related to gambling, seek help from a licensed health professional. This blog is not liable for any losses, damages, or consequences resulting from betting activities.
