Letter from WSC (Royal Military College [Sandhurst, Camberley, Surrey] on the notepaper of 50 Grosvenor Square) to "Mamma" [Lady Randolph Churchill] in which he expresses his concern about a report on the health of his father [Lord Randolph Churchill], asks her to write to him "unreservedly" on the subject, and says that he worries about the effect of anxiety and travelling on her.

Letter from WSC ([Royal Military College, Sandhurst, Camberley, Surrey] on the notepaper of 50 Grosvenor Square) to [Lord Randolph Churchill] in which he discusses his hopes for his results from Sandhurst and for his father's health and worries which he hopes will be "lulled by the land of the lotus" (quoting one of his father's speeches).

Letter from WSC (50 Grosvenor Square [London]) to "Mamma" [Lady Randolph Churchill] expressing shock at a telegram from Madras [India] reporting the deterioration of [Lord Randolph Churchill's] health, and his intention to see his father with "Jack" [John S Churchill]. He bids her to "keep your pluck and strength up" and to write to him.

Letter from WSC (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] in which he describes a horse-riding accident and reports that [John] Milbanke is to join his regiment.

Letter from WSC (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] in which he says that his leg is improving, apologises for not being able to deliver her messages to Sir Henry [Drummond] Wolff or Lord Wolverton, reports that Colonel [John] Brabazon has been ill and asks her to reconsider allowing a horse to run under his name.

Letter from WSC (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] concerning financial affairs in which he details the amounts he has spent and asks her to send him money to buy a charger. He also reports that his leg is improving, that he has ridden in a point to point, comments that he is glad that he has made friends and discusses horse racing and the possibility that a colt may run under his name.

Letter from WSC (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] describing his life at Sandhurst, pains in his eye and a visit to Goodwood [races, West Sussex] where he met "Jim" [James] Lowther, [Alfred Edward, Prince of Wales] and [Lady Beatrice Butler]. He also makes observations on the strength of the Unionist Party and the likelihood that they may split over the issue of Protection.

Letter from WSC ("In camp", 4th (The Queen's Own) Hussars, Bangalore, Madras [India]) to "Mamma" [Lady Randolph Churchill] in which he discusses: the likelihood that he may be posted to Egypt, a recommendation made by the colonel, his intention to return to England if he is not quarantined, sufferings from sunburn and his position as brigade major and adjutant about which he comments "responsibility is an exhilarating drink".

Letter from "Jack" [John] S Churchill (Elstree School [Hertfordshire]) to "Mama" [Lady Randolph Churchill] in which he thanks her for allowing "Woom" [Elizabeth Everest] to visit him, reports that he has been placed top of his form and says that he is sorry to hear that "Winney" [WSC] has a toothache.

Letter from WSC (Jodpore [India]) to "Mamma" [Lady Randolph Churchill] in which he says that he has injured himself and will not be able to play in the polo tournament.

Letter from WSC (Meerut [India]) to "Mamma" [Lady Randolph Churchill] in which he says that he has been able to play in a polo tournament as his shoulder has recovered, that he is staying with Sir Bindon Blood, that he will discuss the title of a magazine with [James] Welldon and will write a preface for it.

Letter from "Jack" [John S Churchill] ([Harrow School, Middlesex]) to "Mama" [Lady Randolph Churchill] in which he says that "Winney" [WSC] is taking "all kinds of medicines" and sends his love.

Letter from [John S Churchill] ([Harrow School, Middlesex]) to "Mama" [Lady Randolph Churchill] in which he discusses arrangements to return home and says that "Winney" [WSC] is unwell.

Part of a letter from "Jack" [John] S Churchill (The Deepdene, Dorking [Surrey]) to [Lady Randolph Churchill] in which he asks after the health of "Papa" [Lord Randolph Churchill].

Letter from WSC (105 Mount Street [London]) to "Mama" [Lady Randolph Churchill] including: his opinion that the government will not be able to continue for much longer, his plans to visit Ivor [Guest, later Lord Ashby St Ledgers and 2nd Lord Wimborne], and electric treatment for his dislocated shoulder.

Letter from WSC (Canford Manor, Wimborne [Dorset]) to "Mamma" [Lady Randolph Churchill] informing her of his decision to remain to continue massage treatment and inviting her to Manchester. He discusses the masseuse's opinion that his speech impediment is caused by a ligament in his tongue and the probability that the government will resign and "CB's" [Sir Henry Campbell-Bannerman] activities.

Letter from WSC (105 Mount Street [London]) to "Mamma" [Lady Randolph Churchill] in which he informs her that Sir Felix Semon has refused to "cut off my tongue" [a reference to WSC's speech impediment which was thought to be caused by a ligament]; discusses an invitation to Blenheim for Christmas; the formation of a new government and the possibility that he might be given office. Envelope present marked "private".

Letter from [George Cornwallis-West] (Keele Hall, Newcastle, Staffordshire) to [Lady Randolph Churchill] in which he recommends that she should visit [Dr Keith] "as I am bad again in fact I always am after having been naughty with you.".

Letter from [George Cornwallis-West] (White's Club [London]) to [Lady Randolph Churchill] in which he says that he has decided not to go to Newlands [Manor, Lymington, Hampshire], discusses domestic matters [at Salisbury Hall] and says that he is sorry that she has decided not to go for a cure.

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.

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.