- 1929: Gale graduated from the University of Toronto where he received his Bachelor of Arts
- 1932: Formally became a lawyer following further studies at the Osgoode Hall Law School
- 1944: Became partner of Toronto legal firm Donald, Mason, Weir & Foulds (today known as WeirFoulds LLP)
- 1946: Designated King's Counsel in 1946
- 30 October 1946: Became a judge for the Trial Division of Ontario's High Court of Justice
- 1952: King's Counsel designation became Queen's Counsel upon the 1952 accession of Queen Elizabeth II
- 1956: Chief editor for what would be known as "Holmestead & Gale", a rewriting of Ontario's court rules
- 1963: Became member of the Ontario Court of Appeal
- 1 June 1964: Became Chief Justice of Ontario's High Court of Justice
- 21 September 1967: Became Chief Justice of Ontario, the province's highest judicial position
- 1968: Joined executive of the Canadian Judicial Council
- 1969: Judicial Council of Ontario is created with Gale as its first Chairman
- 1976: Retired as Chief Justice of Ontario, subsequently joining the Ontario Law Reform Commission as vice-chair
- 1979: Joined the (Ontario) Premier's Advisory Committee on Confederation
From 1956, he also served for a long term on the Board of Governors of Wycliffe College, a Toronto theological school affiliated with the Anglican Church of Canada. He was also active within that church denomination as a member and Churchwarden (1956–1960) of Toronto's St John's York Mills parish.
Gale donated a trophy in 1973 for a competition which is today known as the Gale Cup Moot which demonstrates skills in legal argumentation using staged proceedings.