Rawdon Middleton was born on 22 July 1916 at Waverly in Sydney, a great-nephew of the explorer, Hamilton Hume. His family moved to the western districts of New South Wales when he was young and he attended school in Dubbo, becoming a keen sportsman and later finding work as a jackeroo.

He enlisted in the RAAF on 14 October 1940 under the Empire Air Training Scheme. Having learnt to fly at Narromine, New South Wales, Middleton was sent to Canada to continue his instruction. He reached Britain in September 1941 and was promoted to Flight Sergeant in December that year. In February 1942 Middleton was posted to 149 Squadron, Royal Air Force, and began his operational career. His first operational flights, to the Ruhr, were as second pilot in Stirling bombers but by July he had become first pilot. His first operation as captain of an aircraft was to Düsseldorf.

On 28 November 1942 he took off on his 29th operation, to the Fiat works in Turin, Italy. Middleton's aircraft was struck by flak over the target, one shell exploded in the cockpit wounding Middleton in the face and destroying his right eye. The same shell also wounded the second pilot and wireless operator. Middleton lost consciousness and the aircraft dived to just 800 feet before the second pilot brought it under control. They were hit by more flak as they tried to escape the target.

When Middleton regained consciousness he began the long and gruelling flight back over the Alps towards England, knowing that his damaged aircraft had insufficient fuel to complete the journey. The crew discussed the possibility of abandoning the aircraft or trying to land in northern France but Middleton decided to head for England where his crew would have the chance to bail out. As they approached the French coast the Stirling was again hit by flak but flew on. Now over the English coast with only five minutes of fuel left Middleton ordered the crew to abandon the aircraft. Five men left the stricken plane, and two remained on board to help Middleton before attempting to parachute to safety, although unfortunately both were drowned. The Stirling then crashed into the sea, killing Middleton. He was only one operation away from completing his first tour on bombers.

Middleton's bravery was recorded in the English press and earned him the admiration of the British public and a posthumous Victoria Cross. His body washed ashore at Dover on 1 February 1943 and he was buried in the churchyard of St. John's, Beck's Row, Suffolk, with full military honours