Underhill commissioned from the Royal Military Academy Sandhurst on 7 April 1979, into the Royal Corps of Transport, initially on a short service commission.[3] He was promoted to lieutenant on 7 April 1981,[4] and after spending time as a troop commander in the Gurkha Transport Regiment in Hong Kong,[5] he completed the Regular Careers Course and was once more promoted to captain on 7 October 1985.[6] Upon promotion to major on 30 September 1990,[7] Underhill returned to Hong Kong in command of a squadron, and deployed with the UN as part of the United Nations Peacekeeping Force in Cyprus. After transferring to the Royal Logistic Corps upon its formation in April 1993,[8] he once more returned to Hong Kong as the second-in-command of the newly raised Hong Kong Logistic Support Regiment RLC.[5] Promotion to lieutenant colonel then followed on 30 June 2000,[9] along with the role of overseeing the formation of the tri-Service International Military Advisory and Training Team (Sierra Leone). After a posting at the Defence Transport and Movements Agency; and as Commander of Logistic Support, London District; Underhill was once more promoted to colonel on 30 June 2007,[10] and took up the role of commander the Royal Logistic Corps Territorial Army.[5]
As a staff officer, Underhill served as the Assistant Head for Operational Energy Management of the Defence Fuels Group; Commander, Logistic Support & Infrastructure at 4th Division; and finally as the Assistant Chief of Staff for Support, at Headquarters Support Command.[5] Underhill retired in 2013, at the rank of Colonel.[11]
Underhill has been Deputy Lieutenant of Merseyside since 2019;[12] the Honorary Colonel of 158 Regiment RLC since 2013;[5][13] and the Honorary Life President of the Army Rugby Union since 2016.[11] He was, until his retirement in February 2025, the Chief Executive of the North West Reserve Forces and Cadets Association.[14]
Underhill was appointed an MBE in the 2000 Queen's Birthday Honours.[15] He was further advanced to an OBE in the Operation TELIC honours list in 2003.[16]