The integration of authentic contemporary architecture within sensitive heritage sites is a complex and challenging task. The successful examples are those where the contemporary architectural forms have been carefully designed to form direct and clear relations with the existing historical settings in terms of scale, massing, proportion, material but yet they are distinguished for their uncompromising new characteristics. Sydney, the city itself is a tremendous potential place to study the ‘old and new’ relationships where one can observe numerous good and bad examples of incorporating new designs in old settings in everyday life.