Gregory was a left-handed batsman who bowled slow left-arm orthodox spin. Gregory made his only first-class appearance during the 1913 season for Hampshire against Oxford University. Gregory made a duck and failed to take a wicket.
Gregory served in the First World War as a Rifleman in the 1st Battalion, King"s Royal Rifle Corps, when he was killed at Zonnebeke, Belgium on 27 October 1914, aged 27.
Having no known grave, he is commemorated on the Menin Gate Memorial.