He made his first-grade debut in Sydney district cricket at the age of 16 and proceeded to his first-class debut for New South Wales at the age of 20 in 1928–29. In 1931–32, Fingleton gained a regular position for New South Wales. He then made his debut in the Fifth and final Test of the season against South Africa, making 40 in an innings victory. The following season, Fingleton won praise for an unbeaten century against the bodyline attack in a tour match despite suffering multiple bruises and being accused of leaking the infamous verbal exchange between Australian captain Bill Woodfull and English manager Plum Warner during the acrimonious Ashes.