[6] In 2015, Montgomery began attending the University of North Carolina at Charlotte, where he played for the men's soccer team.
[23] From 2016 to 2018, he played with the Victoria Highlanders in the Premier Development League, captaining the side in his final two seasons.
[24] In 2016, he was named Lake Side Buoys Supporters’ Choice Award as the Highlanders’ player of the year.
[40] In June 2021, he was loaned to USL Championship side San Diego Loyal SC for the rest of the 2021 season.
[50] In 2020, he was officially named to the Canada U23 team for the 2020 CONCACAF Men's Olympic Qualifying Championship,[51] later being re-named to the squad in March 2021 (as the tournament was delayed from 2020 due to the COVID-19 pandemic.
[52] He made his debut in the first group game against El Salvador, where he suffered an injury, returning in the semi-final loss to Mexico.