 DiPierdomenico was born in Hawthorn to parents Stefano and Antonietta, who had emigrated to Australia from Abbateggio, Italy.A hyperactive child who suffered from stuttering, Dipper attended numerous schools in Hawthorn and neighbouring areas, including Kew High, where he met his future wife Cheryl Bayley, and Swinburne Tech, where his headmaster was his future Hawthorn coach, John Kennedy Senior, DiPierdomenico began playing football in his early teens for local clubs East Hawthorn and North Kew before signing for VFL club Hawthorn as an eighteen-year-old.Beginning his career with the Hawthorn Football Club in 1975, DiPierdomenico started slowly, playing 99 reserve-grade games as he flitted between first team and reserve-grade football.