DiPierdomenico was born in Hawthorn to parents Stefano and Antonietta, who had emigrated to Australia from Abbateggio, Italy. A hyperactive child who had a stutter, 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.
AFL career
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. He kick-started his career in 1978, culminating in a best-on-ground performance in the 1978 VFL Grand Final. DiPierdomenico was initially assigned guernsey number #53, but subsequently wore number #9. Typically, he was considered one of Hawthorn's best players. He was known for his toughness, and the moustachioed Dipper was one of the much-loved, and most media-covered characters in the VFL during the 1980s. DiPierdomenico won the Brownlow Medal, in 1986 tying with Greg Williams, who was playing for Sydney at the time. During that season, DiPierdomenico was considered very fortunate to have avoided the AFL tribunal, and consequent ineligibility for the Brownlow. Later in the week, he would win his third Premiership medallion as the Hawks defeated Carlton by 42 points. Late in the first quarter of the 1989 VFL Grand Final, DiPierdomenico was running backwards to take a mark when he was met solidly from behind by Geelong star Gary Ablett. The force of the collision broke several of DiPierdomenico's ribs and punctured one of his lungs. Despite the pain, and being unaware of the extent of the damage, DiPierdomenico continued to play until the final siren. He collapsed shortly after the game and was rushed to the casualty ward of St. Vincent's Hospital, where doctors found out that DiPierdomenico had punctured a lung. He recounted the gravity of the situation years later:
"By this time I'd been shifted into intensive care. The doctor came in and said if they didn't gag me I was gone... So there you are. I had eight days in hospital to think about what might have happened. To tell you the truth, it scared me."
DiPierdomenico went on to play 240 games and kick 130 goals with the Hawks, retiring in 1991, and participating in five-day and five night premierships during one of the most successful eras that a VFL/AFL club has ever achieved. It is said that Dipper was spotted out drinking in Galway, Ireland in 2004, after he oversaw a heavy International Rules loss by his own team. He was reportedly very drunk and rather abusive towards fellow countrymen.
After DiPierdomenico retired, he became a popular media personality as a boundary rider with the Seven Network. After Seven lost the rights to broadcast AFL in 2001, DiPierdomenico continued his tradition as a boundary-rider on radio station3AW. In the 1990s, DiPierdomenico made an appearance, along with Dermott Brereton and Adrian Barich, in a charity rugby league match and scored a try, and in comedic fashion dived over the line in a fashion similar to Superman to celebrate. In 2010, he was stood down from his role in the Auskickjunior development program after making a racist remark regarding Gavin Wanganeen. DiPierdomenico made a cameo in TV series Neighbours in 1999, and he appeared on the Channel 9 weight-loss show Excess Baggage in 2012. He also hosted a TV series in 2019 called "Dippers Backyard BBQ Wars".
