Private Harry Flitcroft enlisted The Cameronians (Scottish Rifles) prior to volunteering for airborne forces at the formation of 1st Parachute Brigade. He undertook the 1st advanced training course at RAF Ringway 4 to 11 January 1942. The first advanced training course involving a night descent from a balloon and aircraft descents with arms containers.Later, in February 1942, Pte Flitcroft took part in the Bruneval raid, a daring parachute operation tasked with capturing components from a German radar system in enemy occupied France and bringing them back to the UK for British scientists to examine.

Pte Flitcroft was part of Jellicoe Section under the command of Lieutenant Peter Young and Sergeant Gregor McKenzie, and flew to the drop zone in a converted Whitley bomber (Nu 9127). The raid was a complete success.

He then saw active service in North Africa (Operation Torch), Sicily and Italy before returning to the UK in November 1943.

Pte Flitcroft jumped into Arnhem on Operation Market Garden on 17 September 1944, as a sniper with 7 Platoon, C Company, 2nd Para Bn. He was later taken a Prisoner of War.