Sheckleford signed for the Spireites last summer after leaving Maidenhead. He started his career with Fulham, playing for the under-18s, under-19s, under-21s and under-23s. The right-back was part of the Fulham squad that reached the 2014 FA Youth Cup final, losing 7-6 on aggregate to Chelsea. He gained some first-team experience at Wealdstone in 2016 before leaving Craven Cottage in 2017. After a year out of football, Sheckleford joined Maidenhead.