In 1892 he was appointed judge's associate to his father, and on 10 August 1894 he was called to the Bar. In 1917 he was appointed King's Counsel and he acted as a Supreme Court judge from November 1936 to February 1937.[3]
Windeyer appeared in many notable cases, significantly for Percy Brookfield, Thomas Mutch and Ernie Judd in 1918 when they appealed against the conspiracy trials of members of the Industrial Workers of the World in 1916. He was also counsel in the Australian Newspaper Proprietors' Association's successful case against Arthur Calwell's censorship laws during World War II. He retired in 1946.[3]