[1] In 1937 Winskill joined the Royal Air Force Volunteer Reserve and trained as a pilot.
Shortly after joining 603 Squadron, he scored his first aerial victory when he shot down a Messerschmitt Bf 109 over Dungeness, Kent,[1] on 29 October 1940.
[1] With the squadron he flew fighter sweeps and bomber escort sorties over Nazi occupied France.
[3] On 14 August 1941, he was flying over France escorting bombers whose target was the St Omer railyards near Lille.
[1] However, in the dogfight with the remaining Nazi fighter, his Spitfire sustained damage and burst into flames.
[3] He landed safely and a French farmer immediately ushered him to a cornfield where he hid until nightfall.
[1] The farmer' son, Felix Caron, then arrived to bring him to the safety of their farm in Saint-Folquin.
[1] As flying over Europe was forbidden to those who had used a Resistance escape route for fear that if captured they would divulge the information, Winskill was posted to an air defence squadron in Scotland.
[1] He was then appointed as the Officer Commanding of the Pilot Gunnery Instructor Wing of the school, a post he served in between March 1944 and December 1944.
[10] Winskill continued his military service after the war ended and he was given a permanent commission in the Royal Air Force on 1 September 1945 in the rank of squadron leader.
[3] In 1961, Winskill was appointed Group Captain Operations at the headquarters of Royal Air Force Germany.
[17] In that role he did not fly the aircraft but was responsible for the safety and comfort of the Royal passengers in addition to commanding the flight.
[18] His arrival coincided with the introduction of the Westland Wessex helicopter and the Hawker Siddeley Andover aircraft to the Flight.
[1] In July 1971, he oversaw the first parachute jump by an heir to the throne when Charles, Prince of Wales completed one over the Channel.
[19] His citation read: This officer has carried out over 250 hours operational flying and has destroyed at least 3 enemy aircraft.
He destroyed one of the enemy fighters and his action certainly saved the bomber from serious attack.On 27 July 1943, he was awarded a further Distinguished Flying Cross.
[21] In the 1973 Queen's Birthday Honours, he was appointed Commander of the Royal Victorian Order (CVO).
[22] In the 1980 New Year Honours, he was promoted to Knight Commander of the Royal Victorian Order (KCVO).