[3] Once out of office, Ainlay made his first bid for mayor in the 1936 election, finishing third of five candidates as incumbent Joseph Clarke was re-elected.

He made two subsequent unsuccessful attempts to return to aldermanic office (in the 1937 and 1938 elections) before taking three years off from municipal politics.

He was re-elected in 1943, but resigned halfway through his two-year term to run for mayor in the 1945 election, when he defeated Winslow Hamilton.

[5] Harry Ainlay did not seek re-election in the 1949 election, due to health issues arising from a serious fall he had sustained working on his retirement home in BC.

He finished second of five candidates, ahead of incumbent Liberal MP Cora Taylor Casselman but still being defeated by Social Creditor Patrick Ashby.

He finished second of four candidates, ahead of incumbent Progressive Conservative Roderick Charles MacDonald, but being defeated by Lyle Wicks of the British Columbia Social Credit League.

He left an endowment for a $500 scholarship to be given in his name to a graduating student planning on pursuing a career in Education.