Sidney is a boys' boarding House for pupils aged 13-18, and is one of the School's four Field Houses located on Milton Road, facing the playing fields to the rear. The front of the House has a beautifully secluded front lawn which often plays host to barbecues, charity events or croquet. Every pupil’s behaviour, attitude and conduct within House is fundamental to bonding the community together and making it thrive. The Sidney House motto is “Your need is greater than mine”, epitomising the spirit of brotherhood and care and support of others.

Housemaster, Dr Laura MacKenzie, was born and educated in Scotland, but has made England her home since 2011. Having previously taught at the University of Leicester and Leicester High School for Girls, Laura joined Oundle in 2018 as a teacher of Government and Politics. Laura is Head of Trivium and is involved in the Debating Society. Making up the team at Sidney are Deputy Housemaster, Mr Carlos Botana (Arabic), Matron, Mrs Lilian Penlington, and a team of dedicated Tutors.