From Headmasters to Principals, Wenona has had very strong leadership at the helm of the School. The following is the list of these women who have remained committed to the School's motto Ut Prosim, that I may serve. 

The school was lead by Headmistresses Hooke, Messiter, Ralston, Mills, and Jackson. Then came Principals Hadley, Wilde and Scott.

Edith Hooke (Woodstock 1886-1913; Wenona 1913-1919)

Dorothy Messiter (01/02/1920-31/06/1920)

Edith Ralston (01/07/1920-1963)

Francis Mills (1964-1966)

Barbara Jackson (1967-1994)

Margaret Hadley (1995-2007)

Denise Thomas, Interim Principal (07/2007-12/2007)

Dr Kerrie Wilde (2008-06/2010)

Dr Elizabeth Guy & Julie Wiseman, Acting Principals (07/2010-06/2011)

Dr Briony Scott (07/2011-12/2024)

Linda Douglas (commenced 01/2025)