Montgomery was undrafted out of high school, therefore he joined the University of Maine and played 4 years with the team, winning numerous awards and establishing himself as one of the best prospects in hockey. Most notably he was named an All-Star 3 years (1991, 1992, 1993) and was named NCAA Tournament Championship MVP when he captained Maine to a record of 42–1–2 and the 1993 National Championship. His three third-period goals lifted the Black Bears to a 5-4 comeback win over Lake Superior State in the title game. Montgomery finished his career at Maine as the school's all-time leading scoring with 301 points on 103 goals and 198 assists. His number 19 was retired by Maine, one of three players who have that honour, the others being Hobey Baker Award winners Scott Pellerin (#8), and Paul Kariya (#9).