She began taking riding lessons at age nine, and after finishing high school in Brampton, she studied equine management at Kemptville College, part of the University of Guelph.
In 2007 aboard Mike Fox, Wilson became the first woman to win North America's oldest and Canada's most important race, the Queen's Plate.
[1] In 2015, Wilson won the Shergar Cup alongside teammates Sammy Jo Bell and Hayley Turner, marking the first victory for an all-female side in this event.
[4] In 2018, she became just the second woman to win the Avelino Gomez Memorial Award, given annually to jockeys who have made significant contributions to Canadian thoroughbred horse racing.
In October 2024, Wilson suffered a neck fracture and shattered her pelvis when her mount Ready Shakespeare fell due to an apparent cardiac arrest.