Born at Chesterfield in 1887 and was on the Trent Bridge ground-staff from 1905 to 1907, but never played for Nottinghamshire. He subsequently enlisted in the King's Royal Rifles and his slow left-arm bowling gained many wickets in military matches. He came to Hampshire's notice at Aldershot on May 16, 1913, when, playing for the King's Royal Rifle Corps, he took all 10 wickets of the 2nd Worcestershire Regiment for only 15 runs. As a result, a few weeks later he played in one match for Hampshire against Oxford University at Southampton, but unfortunately for him it was remarkable for the aggregate of 1,477 runs for 32 wickets - the second highest aggregate for any match in England at that time. Gregory's match figures of 0-87 were in stark contrast to his 10-15 of just weeks before. A year later the Rifleman was dead: killed in action near Zonnebeke, Belgium, on November 27, 1914, aged 27.