Born in Caringbah, New South Wales, Australia, Robbie "Maddo" Maddison began riding motorcycles at just four years of age. By 12, he had become the New South Wales Amateur Motocross Champion, going on to win numerous state and national titles throughout a successful 10-year motocross racing career.
In 2002, Maddison transitioned to freestyle motocross. Within just a few years, he had established himself as one of the sport's most dominant riders, claiming the prestigious King of the Coast title three consecutive times, he then won King of FMX at The Planet X summer games, dominating FMX in Australia before taking his talents to the world stage.