Rupp's childhood ice hockey teams included the Parma Heights Wings Municipal Hockey Club, where he started playing at age nine. He attended and played for St. Edward High School, a catholic college preparatory school in Lakewood, Ohio. In just two years playing for the varsity squad at St. Edward, the team won two state championships in 1994 and 1995. After winning the Stanley Cup with the Devils, Rupp traveled to SouthPark Mall in Strongsville, Ohio, to display the Cup and sign autographs for fans in his home state.