The mode of mayoral election has remained unchanged from 1860 – annual election by the councillors. From 1860 to 1867 the term chairman was used for the position and from 1868 the term mayor.
Nine councillors were elected to represent the municipality of Woollahra at the elections held in May 1860. The newly elected councillors chose the first mayor (known as the chairman) of the municipality at their initial council meeting held in June 1860. The new position of town clerk of Woollahra Council was advertised and the successful candidate was selected by the councillors in July 1860.