[2] Willsmore attended Prince Alfred College where, as a hard-hitting right-handed batsman and right arm leg spin bowler, he captained the first XI in 1907 and 1908,[3] and then studied at the University of Adelaide, graduating with a Bachelor of Science in December 1916.

[3][5][6] After graduating from Prince Alfred College, Willsmore joined South Australian Grade Cricket League club West Torrens for the 1908/09 season, and in his first match, against Glenelg, made 161 not out.

"[14] Following the resumption of cricket at the end of World War I, Willsmore transferred to Adelaide grade club Sturt as captain[3] and returned to the South Australian team.

Referring to this innings, a journalist wrote "Hurtle Willsmore was a hard, but not wild hitter, and this demoralising burst of hitting was the result of perfectly timed strokes.

[18] Following his university graduation, Willsmore was appointed inaugural senior master in mathematics and physics at Adelaide's then new Scotch College in January 1919.

[20] Willsmore also initiated an annual cricket competition between Scotch, Hale School in Perth, Western Australia and Melbourne's Haileybury College.