Headmasters of Collingwood School
- David Mackenzie
- David Mackenzie was Collingwood School's first headmaster. A former member of the British Navy and an avid rugby fan, he also re-founded Brentwood College on Vancouver Island.
- Graham Baldwin
- Graham Baldwin was Collingwood's headmaster during its formative years. During his tenure, the school population grew from 200 to 1000 students, and was separated into two campuses.
- Jim Burnett
- Jim Burnett was appointed acting Headmaster following the departure of Graham Baldwin. He was previously a member of the US Olympic track & field team.
- Rodger Wright
- Rodger Wright is the current headmaster of Collingwood School, appointed in 2004. He previously served as the Headmaster of Trinity College School in Port Hope, Ontario.
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“True it is that she who escapeth safe and unpolluted from out the school of freedom, giveth more confidence of herself than she who cometh sound out of the school of severity and restraint.”
—Michel de Montaigne (1533–1592)