He achieved eminence early in his career after earning the 2009–10 FIS World Cup Rookie of the Year award.

[6] Kingsbury continued his breakthrough season with one more World Cup event win and five additional medals, finishing the 2010–11 FIS Freestyle Skiing World Cup season 4th overall and 3rd in the moguls discipline, behind countryman Alexandre Bilodeau and winner Guilbaut Colas.

In the midst of this season, he competed in his first 2011 FIS World Championships and began with a bronze medal in the moguls event behind Bilodeau and winner Colas.

[7] In the dual moguls event, Kingsbury fell in the final pairing, again finishing behind Bilodeau, this time for the silver medal.

[9] While the streak ended with a second-place finish in the next event, Kingsbury became only the second man to podium at every FIS freestyle competition in a season, with eight golds, four silvers, and a bronze.

He again failed to beat him, but this still left him as the silver medalist completing a second double medal World Championships.

At the age of 21, Kingsbury defeated Bilodeau in the final for his 21st career win, in the process moving him past childhood role model Jean-Luc Brassard for most World Cup wins by a Canadian (during this same event, Bilodeau's silver medal tied Brassard for most World Cup medals by a Canadian).

"[18] Kingsbury answered this question with what the Canadian Freestyle Association considered to be "arguably one of the most prolific and impressive seasons in freestyle history,"[19] punctuated by a 19–16 victory over teammate Philippe Marquis in the dual moguls finals of the 8th event of the World Cup season in Tazawako, Japan.

[19] This win was also the 28th FIS Freestyle Skiing World Cup victory of Kingsbury's young career, tying him with Frenchman Edgar Grospiron for first on the all-time list.

Kingsbury also finished the day with the moguls and Freestyle overall crystal globes for the fourth straight season.

This was the first time a country has swept the podium in the history of the dual moguls event at the World Championships.

[22] His 2nd place showing still ensured that his streak of six consecutive podium finishes at the World Championships would continue.

Kingsbury had to wait nearly nine months for another opportunity to set the men's record for World Cup moguls skiing victories.

[1] During the 2016–17 season, Kingsbury became the first skier to sweep the single and dual moguls competitions in Deer Valley for a second time.

[24] On December 11, Kingsbury was rewarded for his record-setting season when he was awarded the Lou Marsh Trophy, honouring Canada's top athlete of the year.