 Pentney left the Magpies at the end of the 2018–19 season.On 21 May 2019, Pentney rejoined Chelmsford City for a fourth spell.On 9 November 2019, following a 2–2 draw at home to Dorking Wanderers, Chelmsford announced Pentney's retirement after taking up a full-time role at Ipswich Town.