[3][4] His father became quartermaster for the 3rd Militia Battalion on 1 April 1878,[5] and the family resided at Hounslow Barracks at the time of the 1881 census.

[6] Masterson enlisted at Aldershot in the Royal Irish Fusiliers on 25 August 1881,[1] and served in the 1882 Anglo-Egyptian War, including the Battle of Tel-el-Kebir.

[7] Masterson was 37 years old, and a lieutenant in the 1st Battalion, Devonshire Regiment, when the following deed took place on 6 January 1900, at Wagon Hill, Ladysmith, South Africa for which he was awarded the VC: During the action at Wagon Hill, on the 6th January, 1900, Lieutenant Masterson commanded, with the greatest gallantry and dash, one of the three companies of his regiment which charged a ridge held by the enemy and captured their position.

His regiment's 1st Battalion had transferred to British India, and Masterson left Point Natal on the SS Ionian in November 1902 to join it at Ranikhet, Bengal Presidency.

[16] His great grandfather, Sergeant Patrick Masterson of the 87th Foot, captured a Napoleonic eagle at the Battle of Barossa in 1811 and was given a field commission;[17][18] this is portrayed in Bernard Cornwell's Sharpe's Fury.

A spectacle akin to a Royal Tournament, The Army Pageant held in 1910 at Fulham Palace, saw a re-enactment of this feat, with Masterson portraying the Sergeant.