Sheckleford joined the academy at Fulham in 2011. He progressed quickly through the academy, making his debut for the under-18s as a 15-year-old. He was part of the team that reached the FA Youth Cup final in 2014, and went on to captain the under-18 side. In October 2014, he signed his first professional contract on a two-year deal. This was extended for another year in summer 2016. In November 2016, he joined Wealdstone on loan, where he played 13 times in all competitions.[3] Fulham released Sheckleford at the end of the 2016-17 season.[4]
Maidenhead United
Sheckleford was without a club in the 2017-18 season, though he did play on trial at Bolton Wanderers in April 2018.[5] He signed for Maidenhead United in August 2018,[6] but spent most of the season out on loan at Walton Casuals. After a brief return on loan to Casuals at the start of the following season, Sheckleford returned to the Magpies and established himself as first-choice right-back, holding down his spot in the side for the next three seasons.[7] He left the Magpies in June 2022 after turning down a new deal. In total, he played 93 games for the Berkshire club.[8]
Chesterfield
Sheckleford signed for Chesterfield on a two-year deal in June 2022.[8]