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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Upon Urbino’s windy hill,
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—William Butler Yeats (1865–1939)