Drury subsequently transitioned to ski cross, rapidly achieving success as the overall Nor-Am Cup champion in mens ski cross in 2015, immediately prior to his FIS World Cup debut in December 2015. His progression in the sport was marked by a series of significant milestones, securing his first World Cup podium with a silver medal in December 2017. This was quickly followed by his first career World Cup victory in Sunny Valley, Russia, in 2018. That same year, Drury made his Olympic debut at PyeongChang 2018, where he impressively placed fourth in mens ski cross.
His ascent continued with a bronze medal at the FIS World Championships in 2019, further solidifying his position among the elite. The 2019-2020 season represented a career pinnacle for Drury, as he delivered four victories and three second-place finishes on the World Cup circuit, ultimately becoming the first Canadian man to win a Crystal Globe in ski cross. Despite sustaining a tibia break in December 2020, he demonstrated remarkable resilience, returning to competition for the 2021-22 World Cup season, where he earned his 13th career World Cup medal with a silver in Nakiska. Kevin Drury continued to represent Canada at the highest level, competing in the Beijing 2022 Winter Olympics where he placed 12th overall in men’s ski cross.
His career is distinguished by a commitment to high-performance sport and a consistent presence on the international podium, marked by multiple World Cup victories and significant Olympic and World Championship placements, making him a formidable figure in ski cross.