Before playing in the NHL, Bailey played parts of 2 seasons with the Alberni Valley Bulldogs of the British Columbia Hockey League (BCHL) and 1 season with the Omaha Lancers of the United States Hockey League (USHL). Bailey decided to play college hockey with the Penn State Nittany Lions. He played parts of 3 years with them and was named to the Big Ten Conference First All-Star Team in 2015.