Montgomery's 129-29 record in his first seven seasons is the best seven-year winning percentage (.816) at Hoover since 1943. In addition, the Vikings enter the 2009-2010 season with a 72-4 mark at home during Montgomery's first seven campaigns.
Of course, numbers like these seemed less mind-boggling and almost commonplace during Montgomery's 19-year stay at Triway High School. His Titan teams averaged 18 wins and only 5 losses for those 19 seasons, adding up to an impressive 342-95 record. His teams won 12 league titles in a row, five district crowns, two AP Poll Championships, and made a pair of state final four appearances in 1988 and 1991.
Prior to beginning his own head coaching career, Montgomery spent three seasons as an assistant to current West Virginia head coach Bob Huggins at Walsh University in North Canton. He helped Huggins coach Walsh to the NAIA title game in 1983. Montgomery's coaching career began in 1978 as the Freshman coach at Springfield Local High School. He spent two years in that role before moving on to Walsh. In 26 years as a varsity head coach, Montgomery has had just one losing season, compiling a 471-124 record.
Coach Montgomery and his wife, Becky (a guidance counselor at Northwood Elementary) currently reside in North Canton. They have three daughters: Annie (22, a recent Mt. Union College graduate), Erin (19, a cosmetologist and aspiring actress), and Leigh (17, the Viking's #1 fan!).