A reliable half back flanker, with an unusual kicking style, Montgomery was a premiership player with North Melbourne in 1977, having missed out on their flag win two years earlier. He won the 1972 Syd Barker Medal for the club's best and fairest player and also represented Victoria in 1978. Montgomery's father, grandfather and cousin also represented the North Melbourne Football Club. Ken Montgomery was one of the youngest players to play a senior game with North Melbourne, when in 1968 he played when he was 16 years old. In later years he was in an administrative role at the club and he currently lives in Echuca where he operates a houseboat company called Murry River Houseboats.