25. UFC 161: Evans vs. Henderson - June 15, 2013, Winnipeg, Manitoba
The UFC made it's Winnipeg debut with UFC 161. Looking back at the card almost a decade later and it seems rather underwhelming to be a pay-per-view card. The results of the card also left a lot to deserve as nine of the 11 fights went to decision. Rashad Evans defeated Dan Henderson by decision in the main event. In the co-main future heavyweight champion Stipe Miocic defeated Roy Nelson. However, it was a good night for Canadian fighters who won six of seven fights.
24: UFC Ottawa: June 18, 2016, Ottawa, Ontario
Following his loss in a title fight against Robbie Lawler, Canadian Rory MacDonald entered the main event looking to get another title fight with a victory. Instead, Stephen Thompson convincingly won the fight and got two straight title fights against new champion Tyron Woodley. This fight would also mark the end of MacDonald in the UFC as he would sign with Bellator following the fight.
In addition to a Canadian in the main event, the rest of the card was filled with Canadians. All five fights on the main card featured Canadians but only Steve Bosse and Olivier Aubin-Mercier won. On the preliminary card, Canadians went 4-1. The lone loss happening in the second fight of the night when Colby Covington defeated Jonathan Meunier.
23: The Ultimate Fighter Nations Finale: Bisping vs. Kennedy - April 16, 2014, Quebec City, Quebec
This season of the Ultimate Fighter featured Canada vs. Australia with the Canadians dominating the competition. Middleweight Elias Theodorou and welterweight Chad Laprise won the tournament defeating another Canadian in the final. In the main event, Tim Kennedy defeated Michael Bisping. While in the opening fight of the main card Dustin Poirier knocked out Akira Corassani.
22: UFC 174: Johnson vs. Bagautinov - June 14, 2014, Vancouver, British Columbia
UFC 174 was another easy victory for Demetrious Johnson during his reign as flyweight champion. The main card was featured a solid lineup of fights but the preliminard card was rather forgetable. Canadians went 4-3 on the card with Rory MacDonald winning all three rounds against Tyron Woodley on the main card.
21: UFC 186: Johnson vs. Horiguchi - April 25, 2015, Montreal, Quebec
The main event of UFC 186 saw Demetrious Johnson submitted Kyoji Horiguchi with an armbar with one second remaining in the fifth round. While Quiniton Jackson and Michael Bisping earned decisions on the main card. The seven fight preliminary card saw Canadian fighters win all seven fights. However, the Canadian winning streak was ended on the main card with Thomas Almeida earning a performance bonus for his knockout of Yves Jabouin.
20. UFC Vancouver: Sept. 14, 2019, Vancouver, British Columbia
The event was headlined by Justin Gaethje, who knocked out Donald Cerrone in the first round. The performance was extremely impressive and helped earned Gaethje an interim title fight in the first event held during the pandemic at UFC 249, where he would defeated Tony Ferguson. The card featured an extremely big upset.
On five days notice local fighter Tristan Connelly took on Michel Pereira, who also missed weight. Connelly won the fight by split decision and earned fight of the night honours. In the opening fight on the main card, Canadian Misha Cirkunov submitted Jimmy Crute in the first round with a peruvian necktie.
19. UFC 240: Holloway vs. Edgar - July 27, 2019, Edmonton Alberta
In the main event, featherweight champion Max Holloway dominated Frankie Edgar in a one sided fight. Holloway picked apart Edgar with his striking. Performance bonuses were awarded to Geoff Neal and Canadian Hakeem Dawodu. While fight of the night went to Deiveson Figueiredo and Alexandre Pantoja. In a fight won by Figueiredo, the future flyweight champion. Canadian fighters had a disappointing night, going 3-4. With all three Canadians on the main card losing.