Myles Montgomery played high school football in Neptune, Florida. He began his collegiate career at Cincinnati, where he redshirted his true freshman season (2021) and saw limited action in 2022. In 2023, Montgomery earned a larger role for the Bearcats, appearing in all 12 games. He transferred to UCF for the 2024 season but was stuck in a relief role behind RJ Harvey. Montgomery took control of the backfield in 2025 as a fifth-year senior and team captain, racking up a career-best 887 scrimmage yards. 

Montgomery is a do-it-all back. Although his size would indicate that he could handle a full workload, UCF and Cincinnati consistently split their backfields. He has good size and a thick, compact frame. His contact balance and short-area burst help him excel on inside runs, where he can squeeze through tight gaps and break arm tackles. He's got enough speed to turn a corner on defenders, but occasionally gets caught in the open field. In his final season, Montgomery showed added skills as a reliable checkdown receiver. His top-end explosion is his main shortcoming, but he has a well-rounded skill set that could make him a late-round target.