Russell Winnicott was born on 28 May 1898, the son of Plymouth Alderman Richard Weeks Winnicott and Anne Smith Winnicott. As a young boy, he went to school at Garfield House Prep School in Plymouth. Later, when Garfield House amalgamated with Alton School, he became a pupil at the newly-formed Mount House Prep School. After passing his Common Entrance, he went to Plymouth College and then, aged fifteen, to The Leys School, Cambridge.

At the start of the war, Winnicott was gazetted as a 2nd Lieutenant in the 5th Battalion, Devon Regiment. He transferred to the Royal Flying Corps in August 1916 and won his wings before joining the 41st Squadron on 10 November 1916 and was then appointed a temporary 2nd Lieutenant.

 Fighting with the RFC in northern France, Winnicott scored his first aerial victory on 6 September 1917 when he used an Airco DH 5 to drive down a German reconnaissance plane out of control. He registered kills throughout September and victories five and six on 30 September made him an ‘ace’. He added to his total again on 18 October and on 26 October 1917, was awarded the Military Cross for his valorous actions. Winnicott's MC citation began: "For conspicuous gallantry and devotion to duty in aerial combats....’ On 29 November 1917, he drove a German two-seater down out of control over Rumilly to become a ‘double ace’ (10 kills).

Russell Winnicott died, aged 19, in a flying accident while in action on 6 December 1917.  He is buried in the Military Cemetery in Varennes, a small village situated some 10 kilometres from Albert and 20 kilometres from Amiens in northern France. On 29 January 1918, he was posthumously promoted to Lieutenant, effective 1 July 1917.