Harold served with the 2nd Battalion in the Tirah expedition of 1897-98 and was awarded a Medal and one Clasp. He served in the South African War of 1899-1902, with the 1st Battalion and Mounted Infantry, Dispatches, D.S.O., Queens Medal and three Clasps, Kings Medal and two Clasps. 

He served as 2nd Lieutenant  for the Sherwood Foresters from the 15th of May 1899 and as Lieutenant from the 19th of March 1899. He landed East London South Africa on the 15th of December 1899 and  served with the “B” Coy mounted Infantry from the 25th January 1900. Harold served as the Captain  4th Battalion for The Lancashire Fusiliers from the 11th of January 1902. He retired on the 21st of January 1903. He served in the 11th Battalion (Men from the Greenwood)  of The Sherwood Foresters (10th June 1915), he took them to France in July 1915, and was wounded a year later near La Boiselle, when he was shot through the chest, and was consequently invalided. Harold resumed command in September 1916 and then returned to England in November 1917 for deployment to Egypt, and handed over the 11th Battalion to Major, Hudson V.C., D.S.O., M.C. He served as Major with the Sherwood Foresters from the 25th of October 1917, and was placed on half pay due to ill health on the 25th of October 1922, he then retired with the rank of Lieutenant Colonel. He served in the 6th Battalion Inniskilling Fusiliers (14.1.1918 to 8.11.1918), the 53rd Battalion Kings Liverpool Regiment (2.12.1918-23.4.1919) and the 51st Battalion Manchester Regiment (25.5.1919-7.10.1919).