He officially enlisted at Bury St Edmunds on the 18th June 1881 for the 30th Brigade. He was described as having a height of 5 feet 6 ¼ inches, grey eyes, dark brown hair and a fresh complexion. In 1882 his father, James Winkfield died, leaving Jemima again a widow.
Robert's Army career began with training, first in the Camp at Lincoln and later in the year at Portsmouth. Here, as most young soldiers did, he had a photograph taken showing off his new, smart uniform.
In 1882 he was posted to Aldershot and then to Ireland. He was to be stationed there, moving round various Camps, for the next 9 years. Being a bright young man he was soon promoted first to Lance Corporal in the Lincolnshire Regiment, and then to full Corporal. In June 1887 he gained a Certificate of Education that stated his attainments as being able to read and write from dictation, including Order Books, and also having
"Requisite proficiency in Numeration and Notation: Reduction of weights and measures: Simple Practice and Proportion: Simple Vulgar or Decimal Fractions: Regimental Accounts."
In 1887 Robert was promoted to the rank of Sergeant and on 23rd July 1888 he qualified as being capable of performing the duties of Regimental Transport Sergeant.
Robert's letters from home were now being written for his Mother, in a different hand, as back in Pentney, Jemima's eyesight had deteriorated. Her new neighbours in the Bake House next door had a daughter, Mary who helped Jemima by writing her letters for her. Mary's parents, Thomas and Mary Anne Callow knew all about Army life. They were each seasoned campaigners in their own right. Mary Callow, having begun writing to Robert Winkfield for his mother, was soon writing on her own behalf. Mary and Robert were married in Pentney in December 1891. Robert was by now a Colour Sergeant. He and his new wife, Mary Winkfield went back to Aldershot and their first daughter, Maud, was born there on February 4th 1893. Robert's Army career was now to take them also around the world. They did not return to Norfolk until 1903, when Robert retired. They then settled in Swaffham, though there were many visits by them and the children, to see Jemima, and Mary and Thomas in Pentney.