In December 1899 Stirling was chief secretary in the conservative Solomon government but this ministry was defeated as soon as the house met.

In 1901 Stirling was elected President of the South Australian Legislative Council, and would serve in the position for a record 31 years.

He continued his interest in sport all his life, pioneering polo in South Australia and captaining the team which twice beat Victoria.

Stirling found his ideal position as president of the council, admirably carrying out his duties; as the years passed becoming a kind of elder brother to the newer members.

[2] His elder daughter Madge Mary Stirling (1887–1940) married Knox Lister Colley (1885 – 7 December 1934) on 28 January 1914.