Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] thanking her for sending him an order [?to permit him to fence] and asking her to visit him on Saturday. In a postscript he informs her that he has won a rifle shooting competition and includes a diagram of the position of his bullets. Includes envelope.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he describes skating on "Ducker" [the swimming pool at Harrow], reports that he has been congratulated [?on passing the Preliminary examination for the army] and asks her to visit him. Envelope present.

Letter from WSC (Bangalore [India]) to "Mamma" [Lady Randolph Churchill] in which he discusses the legal action to be taken over a fraud [perpetrated on them by James Cruickshank], comments on [Henry Dupre] Labouchere and [James] Welldon's opinions [about a scandal in the 4th Hussars in which WSC was implicated], describes his daily routine at Bangalore and says that he is looking forward to a shooting expedition with Hugo [Baring].

Letter from WSC (Bangalore [India]) to "Mamma" [Lady Randolph Churchill] describing his garden and asking her to send him seeds. He also discusses Hubert Crichton and careers in the Foot Guards; the possible expense of going to Egypt [to serve under Sir Herbert Kitchener] and his own regrets about his writings about Cuba and his fear that he may have treated the opinion of the insurgents unfairly.

Letter from WSC (Bangalore [India]) to "Mamma" [Lady Randolph Churchill] in which he says that he is busy as acting-adjutant, that he finds it difficult to find material for his letters and is losing touch with England, discusses polo and his reading and asks her to find him a source of detailed parliamentary history.

Letter from WSC (Bangalore [India]) to "Mamma" [Lady Randolph Churchill] in which he discusses: his disappointment at not being allowed to play in a polo tournament and the resulting unpopularity of Sir Mansfield Clarke; the work of an adjutant and his enjoyment of the position; his own military career and the possibility that he will stay in the army for two more years; and his gardening and reading.

Letter from WSC (Bangalore [India]) to "Mamma" [Lady Randolph Churchill] in which he discusses: the likelihood that he might be chosen to serve in Egypt; his plan to return to England; his reading; the behaviour of the British government in Crete [Greece]; his own disagreement with the Conservative Party and disapproval of [Arthur] Balfour, George Curzon [later Lord Curzon] and the government's foreign policy and the possibility that "Jack" [John S Churchill] may enter the army.

Letter from WSC (Government House, Guindy [India]) to "Mamma" [Lady Randolph Churchill] in which he discusses: arrangements for his return to England during his leave and possible routes; horse racing; and his disagreement with [Arthur] Balfour's policy regarding Eastern powers and Greece. Envelope present.

Letter from WSC (Bangalore [India]) to "Mamma" [Lady Randolph Churchill] including: the postponement of his leave; his decision to visit Sir Herbert Kitchener in Egypt; a request for letters of introduction; discussion of his reasons for wishing to return to England during his leave; financial affairs; reading and his gratitude at receiving copies of the Annual Register.

Letter from WSC (Bangalore [India]) to "Mamma" [Lady Randolph Churchill] including: his injury while playing polo; a list of the books he has read while in India; his method of constructing "a scaffolding of logical and consistent views" through studying the Annual Register; observations on education; and arrangements for caring for "Firefly" [a horse] which he is sending to England.

Letter from WSC (Bangalore [India]) to "Mamma" [Lady Randolph Churchill] in which he outlines his plans for returning to England and describes his eagerness to return to civilisation after "barbarous squalor". He comments on the waste of his time in India apart from that spent reading, the amusement provided by discussions between [Ronald] Kincaid[-Smith] and [Charles] Agnew and his distaste for Anglo-Indian society. Envelope present.

Letter from WSC (4th Hussars [Bangalore] India) to "Mamma" [Lady Randolph Churchill] in which he expresses his hopes for "better fortunes" in the future although he says he does not intend to marry yet. He describes his work drawing maps, discusses the publication [of "The Story of the Malakand Field Force"] and his anxiousness about its reception and informs her that he has decided to go to Egypt as a correspondent during his leave.

Letter from WSC (35a Great Cumberland Place [London]) to "Mamma" [Lady Randolph Churchill] in which he says that he has been hunting with the Quorn with "Sunny" [Charles, 9th Duke of Marlborough], gives the names of those he met and says that he has enjoyed several conversations with Sunny and describes their relationship as "a case of flint and steel".

Letter from WSC (S S Shannon, off Aden [later South Yemen, then part of Yemen]) to "Mamma" [Lady Randolph Churchill] in which he says that he has made progress with his book ["The River War"], reports that the ship's copies of ["The Story of] the Malakand Field Force" are regularly read, and asks her to send him copies of the Annual Register.

Letter from WSC (35A Great Cumberland Place [London]) to "Mamma" [Lady Randolph Churchill] in which he asks her to keep his secrets and those of others, not to bet or play cards as it will bring "the most terrible misery" and to organise a political dinner for him.

Telegram from John Colville [Prime Minister's Private Secretary] (Biarritz [France]) to Private Office passing on message from WSC to John S Churchill asking him to let him know how he is feeling and stating that he has been doing a little painting. Carbon copy. Annotated with John's reply.

Letter from Lord Randolph Churchill to [Lady Randolph Churchill] including his lack of success at fishing and a request that she give orders for WSC's hair to be cut short.

Letter from Lord Randolph Churchill (Auchnashellach [Dingwall, Ross and Cromarty, Scotland] on the notepaper of the India Office) to [Lady Randolph Churchill] including sympathy for the difficulties experienced by Clara [Frewen, earlier Clara Jerome] in childbirth; a message for [Henry] Chaplin; his success at fishing; and the hope that she has provided some entertainment for "Winny" [WSC].