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.