Letter from WSC ([29 & 30 Brunswick Road, Hove, East Sussex]) to "Om" [Elizabeth Everest] in which he says that he is feeling weak and "as if I could cry at every thing".

Letter from WSC (29 & 30 Brunswick [Road] Brighton [Hove, East Sussex]) to "Mama" [Lady Randolph Churchill] in which he says that he is "blessed with that inestimable treasure i.e. 'Good Health'" and that he hopes to improve at his studies and at cricket.

Letter from "Winny" [WSC] (29 & 30 Brunswick Road Brighton [Hove, East Sussex]) to "Mama" [Lady Randolph Churchill] in which he says that he has been suffering from a bad cough and expresses concern about [Elizabeth] Everest and "Jack" [John S Churchill].

Letter from "Jack" [John S Churchill] (Harrow School) to WSC, school news, particularly outbreak of scarlet fever.

Letter from Lord Randolph Churchill, 50 Grosvenor Square, To WSC, on visit to Lord Roberts at Grove Park, also on forthcoming visit of the Prince of Wales to Harrow School. Advising WSC to take care with his diet, "Eating fast, as you do is a fertile source of indigestion & heated blood, producing boils". Also advising him to address him as "Dear Father" rather than "Papa" in future letters.

Letter from Elizabeth Everest to [2 Connaught Place, London] WSC, on his appointment to see Sir William MacCormac, [a specialist in hernia surgery].

Letter from "Woom" [Elizabeth Everest], to WSC, offering sympathy on his toothache.

Letter from Count Charles Kinsky to WSC, thanks for letter. Offering sympathy on having measles.

Letter from Lady Randolph Churchill, Banstead, to WSC, on his toothache, advising him to brush his teeth more frequently, also on the Newmarket races.

Letter from Lady Randolph Churchill, Banstead, to WSC, on his toothache, the Duchess of Marlborough's illness and the Newmarket races.

Letter from Lady Randolph Churchill, 2 Connaught Place, London, to WSC, on his appointment with Sir William MacCormac [a specialist in hernia surgery].

Letter from Lady Randolph Churchill, Banstead, to WSC, sending £1 and complaining about the state of his finances, also on his toothache, complaining that he had had another tooth out ".

Prescription from Dr Robson Roose to WSC.

Prescriptions from Dr Robson Roose to WSC.

Prescriptions from Dr Robson Roose to WSC.

Letter from Dr Robson Roose to WSC, sending tonic and prescription.

Prescriptions from Dr Robson Roose to WSC, with envelopes from Squire & Co. (Chemists).

Letter from "Woom" [Elizabeth Everest], 5 Cranmer Road, [Forest Gate] to WSC, on his toothache and his boils.

Letter from "Woom" [Elizabeth Everest], 5 Cranmer Road, [Forest Gate] to WSC, on his health.

Letter from "Woom" [Elizabeth Everest], St George's Vicarage, Barrow-in-Furness to WSC, advice on his health, and on her stay in Barrow.

Telegram from General Sir Archibald Wavell [Supreme Commander, South West Pacific] to WSC regarding military command in Burma [later Myanmar]: feels disturbed at the "lack of real fighting spirit" shown by troops in Malaya [later Malaysia] and Burma, and lists some causes; comments on Lieutenant-General Thomas Hutton [General Officer Commanding, Burma] and proposal to replace him with General Harold Alexander; refers to own rapid recovery.

Letter from WSC to Sir Charles Wilson [President, Royal College of Physicians, later 1st Lord Moran] thanking him for accompanying WSC to Washington [United States] at short notice.

Notes by Anthony Bevir and John Martin [Private Secretaries to WSC] on contacting Sir Charles Wilson [President, Royal College of Physicians, later 1st Lord Moran]; includes correspondence between Bevir and Wilson.

Letter from [Albert Edward, Prince of Wales](Mar Lodge, Braemar [Aberdeenshire, Scotland]) to [Lady Randolph Churchill] in which he thanks her for copying out a letter by WSC about his escape [from the Boers] which he describes as "most interesting" and says that he hopes that her ankle is better. Envelope present.