[1][2][3] Upon completion of his tertiary education, Stockdale pursued a legal career as a self-employed barrister, specialising in industrial relations.

On 2 March 1985, Stockdale was elected to the Victorian Legislative Assembly as the Member for Brighton, a staunchly held safe seat for the Liberal Party.

In 1989 he contested to be leader of the State Liberal Party which saw him lose after Jeff Kennett resigned.

[4] Stockton is also credited with being the world's first Minister for Multimedia, to which portfolio was added the additional responsibility of Information Technology in 1998.

[5] Upon retiring from state parliament in 1999, Stockdale proceeded to accept positions within the Macquarie Bank Ltd, as Executive Chairman, Asset & Infrastructure Group, as well as the Chairmanship of Axon Instruments Inc.