As an acquisitive art award for painting, the winning artworks in the Mosman Art prize form a splendid collection of modern and contemporary Australian art, reflecting all the developments in Australian art practice since 1947. Artists who have won the Mosman Art Prize include Margaret Olley, Guy Warren, Grace Cossington Smith, Weaver Hawkins, Nancy Borlase, Lloyd Rees, Elisabeth Cummings, Adam Cullen, Michael Zavros and Natasha Walsh.

In 2019 Jane Guthleben is a finalist with her work 'North Shore arrangement with superb fruit doves'. She says of the painting:

This work is based on the 17 century Dutch still life floral works by Rachel Ruysch, which have inspired my large floral compositions. For this work I have researched indigenous flora and birds from the Mosman Municipal area that are under pressure from urban encroachment and weeds.