Canada is a regular feature of the Summer and Winter Olympic Games, rarely coming away without a haul of multiple medals. 

At the Summer Games, Canadians have brought home 71 gold medals and 326 in total, while Winter Olympians have grabbed 77 gold medals and 225 total medals. 

As a rule of thumb, you’d never want to be betting against Canada at the Winter Olympics, but at the 2022 Games, an 11th-place ranking wasn’t the best showing. 

Still, the country has enjoyed many much more decorated outings, which has led to the most successful Canadian Olympians boasting several medals. These are those Canadians who can rank themselves among the very best. 

Penny Oleksiak

Canada’s sole Olympian with seven medals is swimmer Penny Oleksiak.

Having broken into the Olympic team for Rio 2016 as a 16-year-old, she became the first Canadian to win four medals at one Summer Games. 

That year, she won the Lou Marsh Trophy to be hailed as the country’s best athlete and at the 2020 Games, Oleksiak added another three to her impressive haul to become the most decorated Canadian Olympian ever.

Still only 23-years-old, Oleksiak boasts a bronze in the 200m freestyle, 4x100m medley, 4x100m freestyle, 4x200m freestyle, silver in the 4x100m freestyle and 100m freestyle, and gold in 100m freestyle. 

Already, Penny Oleksiak is Canada’s most successful Olympian.

Clara Hughes

There are a few Canadian Olympians with a whopping six medals across Olympic events, but only one of them can lay claim to having won medals at both the Summer and the Winter Olympic Games.

That Olympian is Clara Hughes. With two bronze medals at the 1996 Atlanta Games, competing in road bicycle racing and track racing, the Winnipeg native decided to switch it up at the turn of the millennium.

At the 2002 Summer Olympics, Hughes nabbed bronze in the 5000m speed skating. At Turin in 2006, she won gold in the 5000m and silver in the team pursuit. Back in Canada for the 2010 Vancouver Games, Hughes got another bronze. 

To this day, Hughes is the only Olympian to ever win multiple medals at the Summer Olympics and Winter Olympics. 

Cindy Klassen

Joining Hughes in the six-medal club is fellow Winnipeg-born athlete Cindy Klassen. The speed skater first won bronze in Salt Lake City in 2002, getting on the podium following the 3000m final.

In 2006, Klassen completed her mighty collection by netting five meals. She won bronze in the 3000m and 5000m, silver in the team pursuit and 1000m, and finally, a shiny gold medal in the 1500m. 

With her Turin dominance, Klassen became the only Canadian Olympian to ever win five medals at one Games, and was the first women’s speed skater to get five medals at the Winter Olympics. 

Andre De Grasse

Rounding out the group of six-time Olympic medallists is Andre De Grasse: a man so quick that even the live betting doesn’t bother as his race is over almost as quickly as it begins.

It began with a bronze medal in the 100m and 4x100m relay, along with the silver medal in the 200m in Rio de Janeiro. Next came Tokyo 2020, when De Grasse stood on every podium place.

He won bronze in the 100m, silver in the 4x100m relay, and then he conquered the entire field with his superb 19.62-second run in the 200m. 

De Grasse, Klassen, Hughes, and Oleksiak stand as the most successful Canadian Olympians of all time, and there’s a good chance that Oleksiak will increase her lead atop the medal table.


*Credit for all images in this article belongs to AP Photo*

Ben is very much a sports nerd, being obsessed with statistical deep dives and the numbers behind the results and performances.

Top of the agenda are hockey, soccer, and boxing, but there's always time for the NFL, cricket, Formula One, and a bit of mixed martial arts.