 Pentney signed for Chelmsford City on 12 June 2013.After a brief spell with Braintree Town, in which he made two appearances, Pentney joined Maidenhead United in 2015, and was ever-present over the next three seasons, including promotion to the National League in 2017.After 148 consecutive league games in which he played the full 90 minutes, his streak ended when he was sent off at Havant & Waterlooville in October 2018 and was suspended for the following game.