| Beijing 2022 | Charles Hamelin
Marie-Philip Poulin | Short Track Speed Skating
Ice Hockey | Gold (5000m relay)
Gold | Isabelle Weidemann | Long Track Speed Skating | Gold (team pursuit), Silver (5000m), Bronze (3000m) |
| PyeongChang 2018 | Tessa Virtue & Scott Moir | Figure Skating | Gold (ice dance), Gold (team) | Kim Boutin | Short Track Speed Skating | Silver (1000m), Bronze (500m), Bronze (1500m) |
| Sochi 2014 | Hayley Wickenheiser | Ice Hockey | Gold | Kaillie Humphries & Heather Moyse | Bobsleigh | Gold (two-woman) |
| Vancouver 2010 | Clara Hughes | Long Track Speed Skating | Bronze (5000m) | Joannie Rochette | Figure Skating | Bronze (women’s singles) |
| Turin 2006 | Danielle Goyette | Ice Hockey | Gold | Cindy Klassen | Long Track Speed Skating | Gold (1500m), Silver (1000m), Silver (team pursuit), Bronze (3000m), Bronze (5000m) |
| Salt Lake City 2002 | Catriona Le May Doan | Long Track Speed Skating | Gold (500m) | Jamie Salé & David Pelletier | Figure Skating | Gold (pairs) |
| Nagano 1998 | Jean-Luc Brassard | Freestyle Skiing | | Catriona Le May Doan | Long Track Speed Skating | Gold (500m), Bronze (1000m) |
| Lillehammer 1994 | Kurt Browning | Figure Skating | | Myriam Bédard | Biathlon | Gold (7.5km sprint), Gold (15km individual) |
| Albertville 1992 | Sylvie Daigle | Short Track Speed Skating | Gold (3000m relay) | Nathalie Lambert | Short Track Speed Skating | Gold (3000m relay) |
| Calgary 1988 | Brian Orser | Figure Skating | Silver (men’s singles) | Karen Percy | Alpine Skiing | Bronze (downhill), Bronze (super-G) |
| Sarajevo 1984 | Gaétan Boucher | Long Track Speed Skating | Gold (1000m), Gold (1500m), Bronze (500m) | Robert Wilson | Bobsleigh | |
| Lake Placid 1980 | Ken Read | Alpine Skiing | | Name Not Available | | |
| Innsbruck 1976 | Dave Irwin | Alpine Skiing | | Cathy Priestner | Long Track Speed Skating | Silver (500m) |
| Sapporo 1972 | Karen Magnussen | Figure Skating | Silver (women’s singles) | Name Not Available | | |
| Grenoble 1968 | Nancy Greene | Alpine Skiing | Gold (giant slalom), Silver (slalom) | Name Not Available | | |
| Innsbruck 1964 | Ralf Olin | Long Track Speed Skating | | Name Not Available | | |
| Squaw Valley 1960 | Robert Paul | Figure Skating | Gold (pairs) | Robert Paul | Figure Skating | Gold (pairs) |
| Cortina d’Ampezzo 1956 | Norris Bowden | Figure Skating | Silver (pairs) | André Bertrand | Alpine Skiing | |
| Oslo 1952 | Gordon Audley | Long Track Speed Skating | Bronze (500m) | Name Not Available | | |
| St. Moritz 1948 | Hubert Brooks | Ice Hockey | Gold | No Flag Bearer Selected | | |
| Garmisch-Partenkirchen 1936 | Walter Kitchen | Ice Hockey | Silver | No Flag Bearer Selected | | |
| Lake Placid 1932 | Hack Simpson | Ice Hockey | Gold | No Flag Bearer Selected | | |
| St. Moritz 1928 | Jack Porter | Ice Hockey | Gold | No Flag Bearer Selected | | |
| Chamonix 1924 | Ernie Collett | Ice Hockey | Gold | No Flag Bearer Selected | | |
