Tonbridge has an outstanding reputation as one of the finest cricket playing schools in England. The cricket club is open to all years in the school, and with seven grass pitches and two astro turf pitches all boys can expect to play on top quality wickets, and there are not many better grounds in England than the Tonbridge 1st XI cricket pitch, “The Head” - its position in the centre of the school and right beside the Chapel has helped to maintain the popularity and success of the game at Tonbridge and it is the envy of visiting schools. 

There are 19 teams with regular fixtures, as well as a full programme which involves many other boys in the school. Tonbridge has created a cricket academy for the benefit of the boys in the school: this provides them with regular access to excellent professional coaching from ECB qualified coaches and superb facilities all year round. Facilities available to boys include 5 lanes of cricket nets within the Tonbridge School Centre with full length run-ups (44m long) as well as over 10 outdoor astro turf nets and 15 excellent grass nets, all facilities whose excellence is shown by their current use by Kent County Cricket Club.

Tonbridge maintains an excellent set of fixtures throughout the summer term. It instigated and competes in the prestigious Cowdrey Cricket Cup (named after Tonbridge cricketing great Sir Colin Cowdrey) which also involves Eton, Harrow, Radley, Wellington and Charterhouse as well as hosting an annual cricket festival at Tonbridge which includes Millfield and usually a touring team from South Africa as well as one from Australia.

In 2009 and 2010 Tonbridge won the Cowdrey Cup and Tonbridge has regularly produced very successful teams. The U14 team consistently wins the Oliver (Kent) Cup and thereby at U15 level competes in the Lord's Taverners trophy. In 2012 the U15 XI reached the final of this most prestigious of national competitions. In 2014 the Tonbridge first XI reached the finals of the national schools' t20 competition. Several boys have achieved County representation at their age group level (on average about four players in each age group) and many boys go on to play at a high standard of cricket after school. Tonbridge has produced numerous Test match players and County cricketers and leads the Old Boys’ Cricket merit table.