Pendlebury won the Wynne Prize four times for his landscape paintings with The Chicory Kiln, Phillip Island (1956), Constitution Dock, Hobart (1957), Old Farmhouse (1960, shared with John Perceval's Dairy Farm, Victoria) and Road to Whistlewood (1968).
He was a finalist in the Archibald Prize twenty-four times, including Nornie Gude (Artist) (1944) and Anne and Drew Pendlebury (actress and musician respectively) (1979).
[1][5] In May 1953 Pendlebury won the Dunlop Art Contest, with a first prize of A£300, ahead of Arthur Boyd, for his oil painting, Late Afternoon – Rhyll.
[10] The contest was sponsored by the Dunlop Rubber Company of Australia (later became Ansell) and aimed to "foster contemporary Australian art on aesthetic merits alone".
[9] When exhibited in Adelaide, The Advertiser's Elizabeth Young preferred the watercolour entrants and felt Late Afternoon – Rhyll "completely lacks subtlety and with a slick harshness apes to a certain extent the contemporary approach, while having nothing of its essential spirit".
[13] Pendlebury has won the Wynne Prize for a landscape painting, four times: The chicory kiln, Phillip Island (1956), Constitution Dock, Hobart (1957), Old farmhouse (1960, tied with John Perceval's Dairy Farm, Victoria), and Road to Whistlewood (1968).