The only child of Lily and Tom Montgomery, his upbringing was in Wandsworth Parade and he attended the Royal Belfast Academical Institution. His musical studies were at the Royal College of Music. He studied with Sir Adrian Boult, and later continued to study conducting with Hans Schmidt-Isserstedt, Sergiu Celibidache, and Sir John Pritchard. His early conducting engagements included work at Glyndebourne Festival Opera, as an assistant conductor, assistant choral conductor and rehearsal pianist. He later served on the conducting staff at Sadler's Wells Opera.
In 1973, Montgomery became music director of the Bournemouth Sinfonietta. He was music director of Glyndebourne Touring Opera from 1975 to 1976, and has continued with the ensemble as a guest conductor. In 1985, he became both artistic and musical director of Opera Northern Ireland. With the Ulster Orchestra, Montgomery served as its Principal Guest Conductor, and in September 2006, the orchestra announced him as their Principal Conductor effective in September 2007, the first Belfast-born musician named as the orchestra's Principal Conductor. He concluded his principal conductorship of the Ulster Orchestra at the end of his three-year contract in 2010.
Outside of the UK, in 1975, Montgomery was named principal conductor of the Dutch Radio Symphony Orchestra, and from 1985 to 1989 held the same post with the orchestra under its newer name of the Netherlands Radio Symphony. Later, he was appointed as the director of the Dutch Radio Choir (Groot Omroepkoor). In 1991, he became director of opera studies at the Royal Conservatory in The Hague. He continues to make his home in the Netherlands.
Since 1982, Montgomery has been a regular guest conductor at Santa Fe Opera (SFO). In May 2007, Santa Fe Opera named Montgomery its interim Music Director, succeeding Alan Gilbert. Montgomery's tenure as interim music director concluded after the 2007 season, with the naming of Edo de Waart as SFO's chief conductor effective 1 October 2007. In April 2013, Montgomery was named SFO conductor laureate for the 2013 season.
- "The music detective". Belfast Telegraph. 12 January 2007. Archived from the original on 5 September 2012. Retrieved 2007-09-22.
- Erica Jeal (1999-10-14). "A treasure on tour". The Guardian. Retrieved 2007-05-12.
- Tim Ashley (2003-10-09). "Idomeneo (Glyndebourne)". The Guardian. Retrieved 2007-05-12.
- Alf McCreary (2010-09-03). "Proms stars need leaders to set tone for the future". Belfast Telegraph. Retrieved 2010-09-30.
- Matthew Westphal (2007-07-24). "Santa Fe Opera Names Edo de Waart Chief Conductor". Playbill Arts. Retrieved 2007-07-25.
- Anne Constable, "Santa Fe Opera music director steps down". The New Mexican, 9 May 2007.
- Craig Smith (2007-07-24). "Dutch maestro takes over as chief conductor". The New Mexican. Archived from the original on 2007-09-30. Retrieved 2007-07-25.
- Anne Constable (2013-04-24). "Harry Bicket named new chief conductor of Santa Fe Opera". Santa Fe New Mexican. Retrieved 2013-04-30.
- "No. 59282". The London Gazette (Supplement). 31 December 2009. p. 11.
- Kenneth Montgomery's website
- Biography from the Ulster Orchestra web site
- Interview with Kenneth Montgomery by Maria Nocklin, "Music & Vision" website, January 2006.
| Music Director, Glyndebourne Touring Opera
| Chief Conductor, Netherlands Radio Symphony
| Interim Music Director, Santa Fe Opera
Edo de Waart (chief conductor)
| Principal Conductor, Ulster Orchestra