Greig's military career spanned from 1892 to 1921, beginning with his commissioning into the Loyal North Lancashire Regiment and eventual transfer to the British Indian Army.
He was considered the leading "white" player of the time in India, and in 1898 he made the first double-century to be scored in first-class cricket on Indian soil.
[9] In October 1907, Greig was appointed military secretary to the incumbent Governor of Bombay, Sir George Clarke.
[10] He was promoted to major in November 1910,[11] and was made a Companion to the Order of the Indian Empire in the 1911 Delhi Durbar Honours.
[2] Greig served during the First World War with the 107th Pioneers, acting as a temporary lieutenant colonel from August to October 1918 whilst commanding a battalion.
[14] Following the end of the war, he was promoted to lieutenant colonel in July 1919,[15] and retired from active service in November 1921.
[18] From the early 1890s, Greig was a leading member of the Poona Gymkhana, where he was affectionately known as "Junglee" (a play on his first, middle and last names).
[20] Greig intervened, suggesting to the press that the Hindus would be foolish to deprive themselves of Baloo's bowling talents.
[22] In the 1899-1900 Bombay Presidency Match against the Parsees, he recorded his maiden first-class century, making 184 runs opening the batting alongside Archie Douglas;[23] this was the highest individual score made in India to that point.
His reputation in India was such that Ranjitsinhji wrote a letter of introduction for him to Hampshire, writing "Greig is a better batsman than I am, and is an excellent bowler as well".
[24] His first season for Hampshire was a success, with Greig scoring 1,277 runs at an average of 41.19; he made five centuries,[18] including a maiden double-century (249 not out) against Lancashire at Liverpool.
[29] The composition of the committee reflected the changing balance of power in Bombay, with representatives from the Hindu, Muslim, and Parsis communities.
[29] Greig's first-class cricket was solely played in India between 1911 and 1913, predominantly for the Europeans, though he did also feature for his own personal eleven against the Hindus at the Poona Gymkhana.
[17] When on leave in England, Greig made nine appearances in the 1914 County Championship,[17] before it was curtailed by the outbreak of the First World War.
[30] Despite playing a large part of his first-class cricket in India, Greig was described as "no lover of Indian cricket" by the political scientist and author Ronojoy Sen.[31] This was exemplified in a match between the Europeans and the Hindus in the 1916–17 Bombay Quadrangular Tournament, when he was adjudged out stumped by native umpire Mukundrao Pai.
Upon his return to the pavilion, Greig's protests against the decision continued and led to the game being delayed for thirty minutes.
[19] Of short stature, he was derogatorily remarked by D. B. Deodhar as a "white pygmy", [27] while the cricket historian Vasant Raiji wrote "though slight of physique he possessed strong wrists and uncommonly keen vision, which enabled him to employ a variety of attractive strokes all round the wicket".