Sydney art student Alfred Macdonald completed a pair of paintings to document the changes to Wynyard Square.

Construction of an underground rail system to link the suburban rail network to the centre of Sydney was recommended by a Royal Commission in 1908. The City Circle was delayed by World War I, although excavation for the new tunnels and stations began in 1916. Work recommenced in 1922, with Museum and St James stations opening in 1926. To minimise disruption to road traffic, the new line passed through the city under roadways and public parks.

Connecting Central Station to Wynyard, via Town Hall, the western arm of the City Circle line opened on 28 February 1932, to coincide with the opening of the Sydney Harbour Bridge in March.