Canterbury Boys High School has many alumni who have distinguished themselves in various fields.
Academic
- Emeritus Professor Harry Jocelyn: leading world expert on the classical languages
- Distinguished Professor Dexter Dunphy: internationally recognised expert on the management of organisational change and human resource management
- Ron Reilly: distinguished economics educator and former Chair, HSC Economics Examination Committee
- Professor Alf Pollard: admitted to the Actuaries' Hall of Fame
- Donald R Horne: distinguished academic, social critic and author, best known for “The Lucky Country”
- Professor Sam Carey: geologist
- John Lovering: geologist
- John Coutman: Principal of CBHS, 1980-1984
- Douglas Trathen: Headmaster of Newington College, 1963-1970
- Dr Bruce Leckie: pioneering heart surgeon
- Emeritus Professor Alan Fish: Human Resource Management professional and an academic for over 45 years.
- Emeritus Professor Philip Brown and Senior Honorary Research Fellow in Accounting and Finance at UWA
Entertainment, Media and The Arts
- Phillip Knightley: award-winning journalist and foreign correspondent
- Murray Sayle: distinguished foreign correspondent
- Fred Brown: author, most notably “Fred Brown's School Days”
- Geoffrey Parsons: one of the world's greatest piano accompanists
- Grahame Bond: better known as 'Áunty Jack' – Australian comedian and actor
- Bill Collins: the iconic ‘Mr Movies', teacher at CBHS, lecturer at Sydney Teachers' College
- Trevor Sinclair: travel journalist, host of television show "Connections"
- Eddy Meyer: television reporter
- Bryan Davies: singer and entertainer, hosted “The Bryan Davies Show” (ABC TV, 1962-63)
- Lucky Starr: known as Les Morrison, singer and entertainer
- Russ Walkington: breakfast announcer on 2UW
Medicine
- Dr Don Sheldon: distinguished surgeon
- Emeritus Professor Kim Oates: distinguished paediatrician
- Dr William McBride: surgeon and medical researcher
- Dr Bertram (Man-Fai) Ng: leading international hair transplant surgeon
Politics, Public Service and Law
- John Howard: Prime Minister of Australia, 1996-2007
- Graham Alliband: former Ambassador to Vietnam
- Ken Gabb: MLA for Earlwood, 1978-88
- Doug Swan: NSW Director General of Education,1977-85
- Sir John William Goodsell: former chairman of the Public Service Board
- James (Jim) Cameron: MLA for Northcott, 1968-84
- Keith Pearson: Director of the National Archives of Australia, 1970-71
- Eric John Shields QC: barrister; former Senior Public Defender, NSW Frank Sleeman: Lord Mayor of Brisbane, 1976-82
- Henry (Harry) Black: expedition leader, inventor and sportsman; recipient of the Coronation Medal, 1953
Religion
- Rev Robert Porter OBE: Anglican Bishop of South Australia, 1970-89
- Professor Raymond Nobbs: Dean and CEO of the Sydney College of Divinity
Sport
- Arthur Morris: Australian Cricket Test captain, 1951-52; inducted into the Sport Australia Hall of Fame, 1992, and the Australian Cricket Hall of Fame, 2001
- Anthony Mundine: boxer and former rugby league player
- Dr George Peponis: Australian Rugby League Test captain, 1979-80; former chairman of the Canterbury Bulldogs
- Ted Glossop: rugby league player, 1951-57; rugby league coach, 1977-88
- Geoff Bugden: rugby league player for Newtown Jets and Parramatta Eels, 1979-86; 1980 Rothmans Medal winner
- David Frith: cricket author and historian; editor of “Wisden Cricket Monthly”, 1979-1996
- Pierre Hola: rugby union player; represented Tonga in the Rugby World Cup, 2003 and the IRB Pacific Nations Cup, 2007
- John Kambas: rugby league player for Parramatta, South Sydney and Cronulla, 1983-88
- Bruce Bourke: swimmer who represented Australia at the 1948 Olympic Games in freestyle and backstroke
- Maxwell Leonard Fuller: 1963 Australian Junior Chess Champion and Australian chess FIDE Master