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Phil Masterton-Smith was involved in two of the closest finishes in Comrades Marathon history, when in 1930 he narrowly lost to the great Wally Hayward. The following year in 1931, he battled against Noel Burree, and crossed the finish line meters ahead to claim Comrades Victory and become the youngest ever Comrades winner at the age of 19. In 1933 Masterton-Smith couldn’t afford the train fare from Cape Town to run the Comrades Marathon, so he cycled over 1700kms from Cape Town to Pietermaritzburg and finished in 10th position.
Tragically Phil Masterton-Smith was killed in action whilst serving for the Natal Carbineers on 5th June 1942 by a mortar bomb, defending the Gazala line during the siege of Tobruk in World War II.