In December 1926, with the general approval of the profession, Woolcock was appointed a judge of the Supreme Court and began his duties on 1 February 1927, although his health was already in decline. Woolcock proved to be an able and hard-working judge, but died suddenly of endocarditis on 18 January 1929.
Woolcock's appointment to the Supreme Court in December 1926, despite his declining health, was widely accepted. He proved to be a capable and diligent judge before passing away unexpectedly from endocarditis on January 18th, 1929.