He played junior hockey with the Hamilton Tiger Cubs and Hamilton Red Wings for four seasons (1957-61). Dillabough broke in to the NHL in the 1961-62 NHL season when he took to the ice for five games with the Detroit Red Wings. The Wings retained his rights for the 1962-63 season but his entire year was spent with the Pittsburgh Hornets of the AHL. In fact he played three years in Pittsburgh, only getting in to the Detroit lineup on four occasions.