Montgomery was selected Conference Carolinas Offensive Player of the Week twice in September and helped lead North Greenville to a 4-0 record in the month. In those four games, he threw for 859 yards, going 50-for-82 and five touchdowns. He added 261 rushing yards and six touchdowns on 41 carries. Montgomery ran for 104 yards and two touchdowns in a come-from-behind win over Charleston on September 11.