It depicts a real robbery committed by bushrangers in 1852 on the St Kilda Road, in what is now the Melbourne suburb of Elwood.

Strutt had lived in Melbourne from 1850 to 1861, and Bushrangers on the St Kilda Road is one of several Australian history paintings he completed after returning to England.

In the early 1850s, bushrangers committed two major robberies in this area, the earliest of which inspired Strutt's painting.

Finally, at sunset, the bushrangers withdrew their guard, mounted their horses which had been tethered in the bush, and rode off in the direction of South Yarra.

The other event took place on 17 March 1853, on the road near Canvas Town,[3] a temporary settlement of tents on the west side of St Kilda Road not far from the city which provided temporary accommodation for the thousands who poured into Melbourne each week during the gold rush in Victoria.

Gold-buyer Edward Ritter and his brother-in-law Samuel Maxwell Alexander were riding in their chaise-cart from St Kilda to Melbourne.

The government offered a reward of £1600, calculated at £200 per head, for their arrests leading to conviction, and the Melbourne police began to round up likely suspects.