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A letter from the Acting Headmaster Michael Stevens to Parents regarding the Quatercentenary Appeal, school trips, the annual Sixth Form Conference, Sports fixtures, and Open Day for prospective parents.

A copy of the portrait of Headmaster Nigel Lashbrook, painted by O.O. Rebecca Haley ('17). The original painting was presented on his last Speech Day.

A policy on the aims of Oakham School, written by the Headmaster Nigel Lashbrook in 2018. Two pages A and B.

Obituary for Spencer Leeson by G. Talbot Griffith. Date is unknown. Four pages A to D.

A prospectus promoting studying at Oakham School in the 1930s. Contents: Staff; Admission; Work; Fees; Optional Payments; Absence & Remission of Fees; Health; Entrance Scholarships; Other Scholarships & Exhibitions; Buildings; Boarding Houses; Holidays & Hours; Games & Hobbies; School Societies; Expenses; Clothes List.

A prospectus promoting studying at Oakham School in 1942. Contents: Trustees & Staff; Foundation & History; The School today; Situation & Surroundings; Premises & Equipment; School Terms, Holidays, Timetable; Chapel Services, Religious Instruction; Curriculum; Libraries; Reports; Boarding Houses; School House, Wharflands, The Junior House; Clothes; Diet & Tuck Boxes; Health; Absence & Leave; Games; Physical Education; O.T.C.; Scouts; Activities outside the classroom; Entry, Fees, Remission of Fees for absence; Optional Payments, Extras; Pocket Money; Scholarships; Leaving Scholarships; Notice of leaving; Expenses; Appointments with the Headmaster; Day Boys; Publications; Old Oakhamian Club. Nine double-pages A to I. Enclosed is modifications to the clothes list due to Rationing in July 1941 (J).

A roll call for School House, Mr. Scriven's, Mr Williams' and the Day Boys in Spring term 1888.