He rode full-time at Prairie Meadows Racetrack between his junior and senior years in high school.

His father is longtime jockey Allan Hill who rode at Fonner Park during his four decade long racing career.

In 2005, Hill was the runner-up to Emma-Jayne Wilson in the Eclipse Award for Outstanding Apprentice Jockey voting.

[citation needed] On July 10, 2010 Hill swept the two $75,000 stakes races on the 75th Anniversary Day program at Suffolk Downs in front of a crowd of 10,310.

[citation needed] Hill officially retired from racing on December 6th, 2022, two years after suffering a severe neck and back injury at Oaklawn Park.