Montgomery played
first-class cricket for
Somerset County Cricket Club between 1901 and 1909. He also played a few matches for the
Marylebone Cricket Club and one each for the
Royal Navy cricket team and a "Gentlemen of England" team; he played in other non-first-class matches for both MCC and the Navy sides. Montgomery was a middle-order right-handed batsman and an occasional bowler whose bowling style is not known. He was educated at
Marlborough College where he played in the annual match at
Lord's against
Rugby School in both 1897 and 1898. He made his first-class debut in two matches for Somerset in 1901. In the first, against the
South Africans he made 1 and 0. He did marginally better a few weeks later with scores of 7 and 8 in the match against
Gloucestershire County Cricket Club. He then made irregular appearances for Somerset until 1909, playing more than a couple of matches only in the 1904 season. In this year he made his only score of 50, reaching that exact score when opening the second innings as Somerset lost heavily to
Sussex County Cricket Club. It was in 1904 as well that he took his only first-class wickets, five in all, with a best return of two for 17 against
Hampshire County Cricket Club. As well as playing odd games for Somerset, he also appeared in most seasons in a couple of matches for MCC, though none of these matches were first-class until 1907. Similarly, he played for the Royal Navy cricket team against the
British Army cricket team from 1908, but the only first-class match in this series he played in was his last first-class match in 1912. ==Military career==