Dean Billingsley was an Exeter City trainee between 2013 and 2015 before leaving to play for Exmouth Town, Bideford and, by 2019. Sidmouth Town. Returning to Exmouth, he was part of the team that won promotion from the Western League in 2022 and subsequently featured for the club in the Southern League in 2022/23. 

As of the start of the 2024/25 season, Dean was appearing for Alphington in the Devon League.