Madison played fours years of
college soccer, including three years at the
University of Virginia and a single year at the
University of Maryland, Baltimore County. Madison also played with
USL PDL side
Reading United from 2013 to 2015. On January 19, 2016, Madison was selected in the fourth round (70th overall) of the
2016 MLS SuperDraft by
Toronto FC. However, he wasn't signed by the club and instead joined PDL side
Kitsap Pumas for their 2016 season. Madison signed with
United Soccer League club
Rochester Rhinos on February 13, 2017. In February 2018, Madison moved to
Geelong, Australia, signing for
North Geelong Warriors FC, a club competing in the National Premier Leagues Victoria 2. Madison started life at his new club by scoring on debut, the winner in a 1–0 win over
Melbourne Victory FC Reserves at
Epping Stadium. Madison finished the season with 13 goals, the third highest tally in NPL2 West. At the club's end-of-season awards night, Madison claimed the Fans' Player of the Year award. ==References==