Grey Cup season. It sneaks up on us every year. Classic games start to play late at night on TSN and ESPN Classic Canada, the playoffs begin, and next thing you know, the championship of professional football in Canada is among us. And here we are.
Watching these classic old games on television got me wondering: Which games were the best ones? Which ones do we remember most? Which games should best be enjoyed by diehard fans of the winning team, and which ones stand out as classics, as enjoyable to watch today as on the day they occurred?
So, I ranked them. The best 29 Grey Cup games of the last 30 years. Why 30? I think I was inspired by the 30th anniversary celebrations this season of the 1991 Toronto Argonauts, and (belatedly) the 1990 Winnipeg Blue Bombers. Plus, these are the ones that I remember. So, here we go.
29. 80th: Nov. 29, 1992, Calgary Stampeders 24–10 Winnipeg Blue Bombers, SkyDome, Toronto
This one was a deeply dull affair, played in a half-empty SkyDome in the hangover of the memorable 1991 season. Doug Flutie won his first of three Grey Cups here, with the Stampeders running up the score 24-0 until the Bombers added some late points to make the final score a little more respectable. Despite featuring incredibly sterling performances from Canadian legends of equal stature Celine Dion and Dave Sapunjus, the less said about this one is probably best.
28. 106th: Nov. 25, 2018, Calgary Stampeders 27–16 Ottawa Redblacks, Commonwealth Stadium, Edmonton
If the most memorable thing about your game involved how poor the artificial turf was, it probably wasn’t a very good one. The Stampeders find redemption after two consecutive Grey Cup losses and avoid the “What could have been” conversation, while solidifying their (still in progress?) dynasty. Had Ottawa pulled off the upset here, giving themselves two wins and a loss in four seasons, would we have to think of them as a dynasty? I don’t think I’m prepared for that kind of what-if situation.
27. 81st: Nov. 28, 1993, Edmonton 33–23 Winnipeg Blue Bombers, McMahon Stadium, Calgary
Winnipeg returns for their third Grey Cup in four years, and despite faring slightly better than the previous season, are once again foiled by a team from Alberta. I was convinced that this loss would lead to the Blue Bombers being labelled the Buffalo Bills of the CFL, which should give you an idea of what my problems were like in 1993. Like the Stampeders’ victory from the previous season, Edmonton got an excellent performance from a CFL legend (Damon Allen, winning his second of three Grey Cup MVP Awards), but the dominance didn’t make for an exciting game.
26. 94th: Nov. 19, 2006, B.C. Lions 25–14 Montreal Alouettes, Canad Inns Stadium, Winnipeg
I had to look it up to remember what happened in this one — probably not a good sign. Dave Dickenson wins the second of his five (and counting) Grey Cups in a game where Paul McCallum accounted for 19 of B.C.’s 25 points. What percentage of his team’s points would a kicker have to account for in order to win the Most Outstanding Player award? Probably 85 percent? Possibly more?
25. 101st: Nov. 24, 2013, Saskatchewan Roughriders, 45–23 Hamilton Tiger-Cats, Taylor Field, Regina
This one turned into a Saskatchewan love-fest pretty early one, which was fun, at least for a quarter or two. Beyond that, this turned out to be a pretty sleepy affair, with the Roughriders and their numerous hometown boys dominating the Tiger-Cats in nearly every facet of the game. Kory Sheets nearly ran for 200 yards behind a stellar group of offensive linemen, all of whom probably deserved to win the Most Outstanding Canadian award.
24. 83rd: Nov. 19, 1995, Baltimore Stallions 37–20 Calgary Stampeders, Taylor Field, Regina
In their mere two seasons of existence, the Baltimore Stallions assembled an incredible array of talent in the coaching and management departments, as well as on the roster, so this victory was probably inevitable. Tracy Ham and the Stallions dominated before moving to Montreal for the 1996 season. You see a lot of players going out on top, but it’s not often you see a team doing it. This game was the first Grey Cup game ever played in Saskatchewan, and most of the game’s drama involved whether or not any fans would be blown into the Wascana by the gale force winds. No casualties!
23. 85th: Nov. 16, 1997, Toronto Argonauts 47–23 Saskatchewan Roughriders, Commonwealth Stadium, Edmonton
Toronto caps off a dominant season (plus-333 point differential!) with a dominant performance in the Grey Cup in one of the game’s great all-time mismatches. Doug Flutie wins his third Grey Cup MVP Award and gives the prize of a new truck away to teammate Paul Masotti. Incredible flex. The other thing I remember about this game is how brown the grass was at Commonwealth Stadium. Can you believe they had natural grass in a stadium in Edmonton for over 30 years?
22. 107th: Nov. 24, 2019, Winnipeg Blue Bombers 33–12 Hamilton Tiger-Cats, McMahon Stadium, Calgary
The Blue Bombers end 29 years of misery with a pummeling victory over the Tiger-Cats, who entered their third decade of Grey Cup futility. This game could go higher on the list if you’re from Manitoba or a big fan of the strip-sack, but Winnipeg dominated from beginning to end. It’s a game that marks an end of an era if you consider what we all had to endure in the following two years, but it’s possible that this marked the beginning of a Blue Bombers dynasty that plays old school football better than anyone has seen in a very long time.
21. 100th: Nov. 25, 2012, Toronto Argonauts 35–22 Calgary Stampeders, Rogers Centre, Toronto
We will probably never fully understand the thought process that led to Ricky Ray being traded to the Argonauts for a package of nothing, but this was probably the result everyone involved was hoping for. Ray leads the Argos to victory in front of a packed house in Toronto in a game that represented the pinnacle of the Argonauts in the new century. This game also featured the debut Grey Cup appearances of Bo Levi Mitchell, Justin Bieber, Carly Rae Jepsen, and Gordon Lightfoot.
20. 99th: Nov. 27, 2011, B.C. Lions 34–23 Winnipeg Blue Bombers, BC Place, Vancouver
On paper this one looked like one of the better Grey Cup matchups in recent memory. The B.C. Lions played strong for all four quarters, while the Blue Bombers concentrated their strong play into only one of them. The Lions took this one at home in a game that featured a Nickelback halftime show, which feels like a comical bit of Vancouver synergy. I guess Ryan Reynolds and Michael Bublé were unavailable for the coin toss and the national anthem that afternoon.
19. 91st: Nov. 16, 2003, Edmonton 34–22 Montreal Alouettes, Taylor Field, Regina
Ricky Ray wouldn’t be denied in a rematch of the previous season’s game. Does it seem to anyone else like literally every Grey Cup in the 2000s was Edmonton-Montreal? Maybe it just seemed that way. Ray bested Calvillo and earned himself an NFL contract, with no small help from a two-touchdown performance from Jason Tucker.
18. 87th: Nov. 28, 1999, Hamilton Tiger-Cats 32–21 Calgary Stampeders, BC Place, Vancouver
The Stamps and Tabbies met again in a Grey Cup rematch, although this sequel failed to live up to the original. Danny McManus and Darren Flutie dominated the Stampeders, now led by the very talented but very green Dave Dickenson. Considering the level of talent on Hamilton this year, it was shocking that they didn’t hoist the cup again within a few seasons, let alone within two decades.
17. 96th: Nov. 23, 2008 Calgary Stampeders 22–14 Montreal Alouettes, Olympic Stadium, Montreal
Does it make sense that this is the last Grey Cup to have happened in Montreal? How have we allowed this to be the case? A post-COVID Montreal Grey Cup one day could be the end of me, I really mean that. Henry Burris won his first MOP award, kickstarted a truly bonkers run of personal success, and sent the second largest crowd in Grey Cup history home unhappy.
16. 95th: Nov. 25, 2007 Saskatchewan Roughriders 23–19 Winnipeg Blue Bombers, Rogers Centre, Toronto
The Roughriders won their first championship in eighteen seasons and the Blue Bombers suffered not even their most painful Grey Cup loss this decade. I couldn’t imagine the pressure on Ryan Dinwiddie, with his first start in the league being the Grey Cup. The Bombers were in this one until the very last minute, remarkably. This was also last Grey Cup appearance for Milt Stegall, who retireed without a ring following the 2008 season. Tragic.
15. 89th: Nov. 25, 2001, Calgary Stampeders 27–19 Winnipeg Blue Bombers, Olympic Stadium, Montreal
This one was a wildly memorable upset by a gritty underdog, or, if you’re from Manitoba, an absolute tragedy. Marcus Crandell played the game of his life to lead the 8-10 Stampeders to the victory, although this one will probably be remembered as the Khari Jones-led Blue Bombers shooting themselves in the foot over and over. That this Winnipeg team never made it back to the championship game still stuns me.
14. 92nd: Nov. 21, 2004, Toronto Argonauts 27–19 B.C. Lions, Frank Clair Stadium, Ottawa
Damon Allen won at age 41 at a time when quarterbacks winning championships in their 40s wasn’t something that happened often in professional football. Pinball also won his first Grey Cup as a head coach, and anytime Pinball is happy, I’m happy. This was maybe the only positive thing that resulted in the brief, tragic life of the Ottawa Renegades: the Tragically Hip played their first and only Grey Cup halftime show.
13. 103rd: Nov. 29, 2015, Edmonton 26–20 Ottawa Redblacks, Investors Group Field, Winnipeg
It remains absolutely shocking that this was the only Grey Cup appearance for Michael Reilly and this Edmonton team (although, as it turns out, things could certainly get way worse!). Ottawa presaged future success by reaching the Grey Cup game in only their second season, but Reilly etched his name in history by besting the tough-as-nails Redblacks defence to get the win.
12. 98th: Nov. 28, 2010, Montreal Alouettes 21–18 Saskatchewan Roughriders, Commonwealth Stadium, Edmonton
The Roughriders entered this one looking to wipe clean the memories of 2009’s devastating loss, but unfortunately for them, Anthony Calvillo was there to greet them. It was the Alouettes defence that really came to play, marking the end of a remarkable run of success for Calvillo and the Als. The Larks haven’t sniffed the Grey Cup ever since.
11. 90th: Nov. 24, 2002, Montreal Alouettes 25–16 Edmonton, Commonwealth Stadium, Edmonton
The first Grey Cup game I attended in person. Not enough credit is given to the Montreal Alouettes for winning this one, defeating a fantastic Edmonton team playing in their home park. We got used to the Alouettes and their dominance after a while but Calvillo was fantastic in this one and the Als won their first title since returning to Quebec six years prior. Another game absolutely loaded with talent and the atmosphere in Edmonton was truly electric.
10. 102nd: Nov. 30, 2014, Calgary Stampeders 20–16 Hamilton Tiger-Cats, BC Place, Vancouver
Another fantastic game overshadowed by one big memorable play, but this one was a great one. Bo Levi Mitchell and Jon Cornish built up a two-score lead before Zach Collaros brought the Tabbies back to within one. And then? The greatest non-play in Grey Cup history. Brandon Banks becoming absolutely despondent on the sidelines remains one of the most compelling images in the history of the game.
9. 93rd: Nov. 27, 2005, Edmonton 38–35 Montreal Alouettes, BC Place, Vancouver
Unquestionably the most chaotic-neutral Grey Cup game of all-time that didn’t involve a ruinous weather event. Edmonton takes the final victory in this best-two-of-three falls contest. Should they have just made this a best of five? I’ll always remember Calvillo in overtime attempting the double pass, Danny Maciocia running out onto the field in celebration before the game was over, and watching the Black Eyed Peas perform “My Humps” while sitting next to my parents.
8. 88th: Nov. 26, 2000, B.C. Lions 28–26 Montreal Alouettes, McMahon Stadium, Calgary
An underrated classic loaded with talent on both teams that marked the beginning of a golden era for the CFL. Montreal fell short in their first Grey Cup appearance since 1979, but they’d make up for it by returning to the game six more times over the next decade.
7. 97th: Nov. 29, 2009, Montreal Alouettes 28–27 Saskatchewan Roughriders, McMahon Stadium, Calgary
I am saying this as a Blue Bombers fan who suffered through five Grey Cup losses and 28 years between victories, but I cannot imagine losing a championship game like this. It’s unfathomable. I would probably not be able to talk about it still, twelve years after the fact. The inexplicable finish often overshadows the game itself, but this one was a back-and-forth classic, with probably the best Alouettes team of that decade emerging victorious, albeit after the most famous second chance in the league’s history.
6. 105th: Nov. 26, 2017, Toronto Argonauts 27–24 Calgary Stampeders, TD Place Stadium, Ottawa
This one was probably the most aesthetically pleasing Grey Cup in a while, with the Double Blue facing off against the Red & White in a picturesque snowstorm in Ottawa. Snow in the Grey Cup: an automatic 10-15 percent improvement (not verified by science). Ricky Ray makes a whole bunch of big plays in his last ever Grey Cup game, stealing the spotlight from Shania Twain and her dogsled. No small feat!
5. 86th: Nov. 22, 1998, Calgary Stampeders 26–24 Hamilton Tiger-Cats, Winnipeg Stadium, Winnipeg
Goodbye Doug Flutie, hello Jeff Garcia. The Stampeders rode Garcia’s arm (and legs) to the Grey Cup, where they met the Tiger-Cats and Danny McManus, who was just a little bit less of a running quarterback. This game was a nail-biter from start to finish with both teams trading field goals until the final play of the game and Mark McLoughlin nailing the field goal for the Stampeders victory. Winnipeg has probably had highest quality of Grey Cup games, on average.
4. 84th: Nov. 24, 1996, Toronto Argonauts 43–37 Edmonton, Ivor Wynne Stadium, Hamilton
This one was played during maybe the darkest days in the history of the league, so we’re incredibly fortunate that it turned out to be one of the liveliest, wildest Grey Cups ever. Ron Lancaster, Don Matthews, Doug Flutie, Gizmo Williams returning a punt for a touchdown: everything you loved about the CFL in the ’90s was in this game, including probably at least a half-dozen drunk guys wearing OUR BALLS ARE BIGGER t-shirts.
3. 79th: Nov. 24, 1991, Toronto Argonauts 36–21 Calgary Stampeders, Winnipeg Stadium, Winnipeg
Almost certainly the most famous game in the history of the CFL, the end of a season about which they’re still telling stories and writing books. In a game featuring Rocket Ismail, DK Smith, Danny Barrett, Chris Schultz, John Candy, and countless other stars on and off the field, the one thing everyone seems to remember is how cold it was that day in Winnipeg (well, that and the beer-throwing guy). This was a tight affair until the fourth, when Ismail took one to the house and showed the CFL just what all the hype was about. I’m not sure we were prepared for the rollercoaster that was the CFL in the 1990s, but this was an exciting preview.
2. 104th: Nov. 27, 2016, Ottawa Redblacks 39–33 Calgary Stampeders, BMO Field, Toronto
This game was marred by low ticket sales and generally bad vibes ahead of the debut of the Grey Cup at BMO Field, and the league desperately needed a great game here. Man, did they ever get a heater. The drama started 30 minutes before game-time, when the Redblacks announced that that guy Henry Burris — you know him? He, uh, might not be able to play. No big deal! Smilin’ Hank powers through a leg issue, starts and goes toe-to-toe with Bo Levi Mitchell for 60-plus minutes. Ottawa managed to outduel Calgary and win Ottawa’s first Grey Cup since 1976.
1. 82nd: Nov. 27, 1994, B.C. Lions 26–23 Baltimore Club, BC Place, Vancouver
I can’t really express the intensity of this situation to anyone under the age of 35, but this game doubled as an expression of national pride comparable to what we’d see for an Olympic hockey tournament. The game itself more than lived up to the pre-game hype, with Lui Passaglia nailing a game-winning field goal with zero time on the clock, probably the biggest play in the history of the league. I don’t know if anyone had considered something like this when the CFL-USA affair was devised, but it was probably the best on-field development to come out of the whole affair. Seriously, make sure to watch this broadcast again if you have a chance — it might be one of the most intense sporting crowds in the history of the country.
