Kelly was an all-city ice hockey selection in high school while playing for Madison East.

However, he said his hockey background may have hurt his golf early in his career because of the aggressiveness it encourages him to bring to his game.

Kelly won the 2009 Zurich Classic of New Orleans with a two-foot par putt on the final hole, beating three players by one stroke (Charlie Wi, Rory Sabbatini, and Charles Howell III).

Instead of going to Q school (where his finish would have placed him directly into the final stage), Kelly played the 2013 season using a career money list exemption, nineteen places higher on the PGA Tour priority ranking list than the 126-150 category (Priority Ranking 29).

In June 2021, Kelly defended his hometown title at the American Family Insurance Championship in Madison, Wisconsin (last held in 2019).