Clifton's 1st XI will play Tonbridge 1st XI at the home of cricket on Tuesday, June 24.
The match, at the Lord's Nursery Ground, marks the centenary of the first time the two teams played each other.
The fixture will have added poignancy against the backdrop of the 100 Years Anniversary of the First World War.
On the day before the 1914 match, Austria-Hungary had declared war on Serbia.
The conflict would take the lives of half the boys playing that day - seven from Clifton and four from Tonbridge.
This is the first time the two teams have met at Lord's since the late 1960s.
Throughout the years, many talented schoolboys made an impression on spectators, including Tonbridge's Colin Cowdrey who would go on to play for England.
However, one in particular, stood out for different reasons. Monty Python's John Cleese played for Clifton in the 1957 match.
It was noted in the Tonbridge school magazine that "the long legged Cleese", who was enjoying his best season as a bowler, "gives the quaint impression of running on stilts."
A precursor to the Ministry of Silly Walks perhaps!