| 5 | Lesley Thompson-Willie | Rowing | Summer | Los Angeles 1984, Barcelona 1992, Atlanta 1996, Sydney 2000, London 2012 |
| 5 | Jayna Hefford* | Ice Hockey | Winter | Nagano 1998, Salt Lake City 2002, Turin 2006, Vancouver 2010, Sochi 2014 |
| 5 | Hayley Wickenheiser* | Ice Hockey | Winter | Nagano 1998, Salt Lake City 2002, Turin 2006, Vancouver 2010, Sochi 2014 |
| 5 | Charles Hamelin* | Short Track Speed Skating | Winter | Turin 2006, Vancouver 2010, Sochi 2014, PyeongChang 2018, Beijing 2022 |
| 5 | Marie-Philip Poulin* | Ice Hockey | Winter | Vancouver 2010, Sochi 2014, PyeongChang 2018, Beijing 2022, Milano Cortina 2026 |
| 4 | Clara Hughes | Road Cycling / Long Track Speed Skating | Summer / Winter | Atlanta 1996, Salt Lake City 2002, Turin 2006, Vancouver 2010 |
| 4 | Émilie Heymans* | Diving | Summer | Sydney 2000, Athens 2004, Beijing 2008, London 2012 |
| 4 | Jennifer Botterill* | Ice Hockey | Winter | Nagano 1998, Salt Lake City 2002, Turin 2006, Vancouver 2010 |
| 4 | Becky Kellar* | Ice Hockey | Winter | Nagano 1998, Salt Lake City 2002, Turin 2006, Vancouver 2010 |
| 4 | Tania Vicent* | Short Track Speed Skating | Winter | Nagano 1998, Salt Lake City 2002, Turin 2006, Vancouver 2010 |
| 4 | Caroline Ouellette* | Ice Hockey | Winter | Salt Lake City 2002, Turin 2006, Vancouver 2010, Sochi 2014 |
| 4 | Meghan Agosta* | Ice Hockey | Winter | Turin 2006, Vancouver 2010, Sochi 2014, PyeongChang 2018 |
| 4 | Rebecca Johnston* | Ice Hockey | Winter | Vancouver 2010, Sochi 2014, PyeongChang 2018, Beijing 2022 |
| 4 | Mikaël Kingsbury* | Freestyle Skiing | Winter | Sochi 2014, PyeongChang 2018, Beijing 2022, Milano Cortina 2026 |
| 4 | Brianne Jenner* | Ice Hockey | Winter | Sochi 2014, PyeongChang 2018, Beijing 2022, Milano Cortina 2026 |
| 4 | Jocelyne Larocque* | Ice Hockey | Winter | Sochi 2014, PyeongChang 2018, Beijing 2022, Milano Cortina 2026 |
| 4 | Natalie Spooner* | Ice Hockey | Winter | Sochi 2014, PyeongChang 2018, Beijing 2022, Milano Cortina 2026 |
