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In 2010, he was stood down from his role in the Auskick junior development program after making a racist remark regarding Gavin Wanganeen.

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 station 3AW.

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".

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 of a VFL/AFL club has ever achieved.

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.

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:

He was known for his toughness (which led to many trips to the Tribunal), 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.

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.

Berto "Robert" DiPierdomenico (born 5 May 1958) is a retired Australian rules footballer who represented Hawthorn in the Australian Football League (AFL) from the 1970s to the 1990s. Popularly known by his nickname "Dipper", DiPierdomenico is one of the most successful Italian Australians to play Australian football, and his contribution to the game was recognized by selection in the VFL/AFL Italian Team of the Century.