Robert enlisted into the Regiment on the 18th June 1892, at the age of 14 years. His first deployment saw him travel with the 1st Battalion from Malta to South Africa to take part in the on-going Boer War of 1899-1902. Whilst there, Robert and the 1st Battalion were involved in numerous battles and served across multiple fronts, notable of which were the battles at Diamond Hill and Johannesburg. For his service in South Africa during this war, Robert was awarded the Queens South Africa Medal with clasps Cape Colony, Orange Free State, Johannesburg and Diamond Hill. He was also awarded the Kings South Africa Medal with clasps South Africa 1901 and South Africa 1902.  

Following the end of the fighting in South Africa and the end of the Boer War, the 1st Battalion were sent to Hong Kong and Robert was amongst them there. In 1902, he was awarded his Long Service and Good Conduct medal.  

Robert was also a committed member of the Army Temperance Society, being awarded some twelve temperance medals over a twenty-year period in recognition for his abstinence