Ranking every Canadian UFC card ahead of UFC 289

5. UFC 206: Holloway vs. Pettis - Dec. 10, 2016, Toronto, Ontario

There was much less hype going into UFC 206 than previous events in Toronto. Weeks earlier the main event between Daniel Cormier and Anthony Johnson was scrapped due to injury. In it's place Max Holloway fought Anthony Pettis for the interim featherweight title after the UFC promoted Jose Aldo from interim to undisputed featherweight champion.

While the hype entering the event was minimal, hype exiting the event was incredible. UFC 206 was one of the best UFC events of all time. Holloway scored a knocked victory. Also scoring great knockouts were Donald Cerrone and Lando Vannata. While the fight between Cub Swanson and Doo-ho Choi earned fight of the night and of the year. In 2022, the fight was inducted into the UFC Hall of Fame. Canadians had a rough night going 2-5.

4. UFC 231: Holloway vs. Ortega - Dec. 8, 2018, Toronto, Ontario

The lead up to UFC 231 was filled with Max Holloway taking over the city of Toronto. Holloway called Toronto the ninth island after the city had embraced him following his performance at UFC 206. In the main event, Holloway fought Brian Ortega, earning fight of the night honors. Holloway scored a TKO after the doctor ruled that Ortega could not continue after his eye swelled shut.

In the co-main event, Valentina Shevchenko defeated Joanna Jedrzejczyk to win the women's flyweight title. Thiago Santos earned a perfomance of the night bonus for his viccious knockout of Jimi Manuwa. While the rest of the card was filled with star power. Canadians went 3-3 on the card.

3. UFC 165: Jones vs. Gustafsson - Sept. 21, 2013, Toronto, Ontario

The main event of UFC 165 between Jon Jones and Alexander Gustafsson will be remember as one of the greatest fights in UFC history. Jones retained his light heavyweight title in a five round war. The fight was inducted into the UFC Hall of Fame in 2021. In the years since the fight, Jones admited that he thought he was going to lose the fight as his partying had gotten out of control.

In the co-main, Renan Barao scored a spinning back kick knockout. While the card also featured a young Khabib Nurmagomedov and Stephen Thompson picking up victories. UFC 165 was a rough night for Canadians who went 2-5.

2. UFC 83: Serra vs. St-Pierre 2 - April 19, 2008, Montreal, Quebec

In the UFC's Canadian debut, hometown hero Georges St-Pierre fought Matt Serra at a sold out Bell Centre. St-Pierre unified the welterweight title after he knocked out Serra in the second round, avenging his loss to Serra at UFC 69. The first card in Canada was filled with star power. On the main card, Rich Franklin and Michael Bisping scored knockout victories.

While on the preliminary card, Demian Maia registered a submission victory and a debuting Cain Velasquez started his UFC career with a knockout. Of the 11 fights, there were nine finishes, including seven knockouts.

1. UFC 129: St-Pierre vs. Shields - Aug. 30, 2011, Toronto, Ontario

UFC 129 might be the most iconic UFC event for Canadian MMA fans. For years, it looked like Canada's biggest province would not legalize mixed martial arts. The UFC hired former CFL commissioner Tom Wright to head it's Canadian operations in May 2010. Within months, Wright as able to get MMA legal in Ontario, leading to the remaining provinces to legalize the sport.

The UFC booked Toronto's Rogers Centre for it's Ontario debut with Georges St-Pierre headlining. In front of 55,724, St-Pierre defeated Jake Shields. The card was stacked. Jose Aldo retained his title against Mark Hominick and Lyoto Machida knocking out Randy Couture on the main card. While the feature prelim saw Rory MacDonald defeat Nate Diaz. Canadians went 6-4 on the card.