In February 2008 a Challoner's team won the regional round of the Oxford Union schools' competition, overcoming 32 grammar and independent schools to make it to the national finals. The school's record in the Oxford competition in particular is excellent; with at least 1 team breaking to finals day almost every year. In the 2008–09 academic year the school also came 5th (out of 48 teams) in the UCL senior competition and in the Oxford finals in the same year reached the top 15 to make two of the school's debaters eligible for England trials in the autumn term of 2009.