Youth and college Hackshaw played on the collegiate level at Arima North Secondary.
Professional Hackshaw played for
North East Stars F.C. in the
TT Pro League since season 2014/2015 and scored 2 goals in his first season. In 2016, Hackshaw signed with American club
Charleston Battery. On 13 December 2018, Hackshaw was signed by
Indy Eleven. He was released by Indy Eleven on November 30, 2022, following the conclusion of the 2022 season. On 23 February 2023, Hackshaw joined USL Championship side
Oakland Roots. ==International career==