Chester Bennett served as a prefect in 1936, was Captain of the School in 1937, and represented the school three times in intercol athletics and four times in intercol cricket. He played six first class matches for South Australia as a middle order batsman and two for Western Australia.
A teacher by profession, Bennett taught at Princes from 1940 to 1943 and from 1954 to 1979. It is as coach of the Princes Ist XI and Ist XVIII for 22 years that Chester Bennett is best remembered. During this time he coached old scholar cricketers of the calibre of Ian, Greg, and Trevor Chappell, Tim May, Ashley Woodcock, and Rick Darling. In football his old scholar successes included All Australian players Peter Darley, Robert Day, and Rick Davies.
He was highly regarded for possessing the qualities of fairness, moderation, dedication, determination and good sportsmanship. Chester Bennett was summed up by Ian Chappell in the phrase ‘He was a wise man; wise in sport and wise in life’. Greg Chappell stated, ‘I never heard him raise his voice once. He understood school boys so well. This was his greatest strength.’