Letter from WSC (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] in which he expresses his approval of her plan to visit Switzerland with "Jack" [John S Churchill]; describes the "mental stagnation" caused by life in the army, which he alleviates by reading speeches by [Lord Randolph Churchill], his intention to study economics or modern history, and a meeting with [Henry] Norris.

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 (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] in which he says that he is looking forward to his toy theatre arriving, requests equipment for it and asks for money.

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 (The Head Master's, Harrow School [Middlesex]) to "Mamma" [Lady Randolph Churchill] promising to give up smoking for six months, reporting that "Jack" [John S Churchill] is "very low" and describing the decoration of his room. Illustrated with drawings of Harrow school boys and uniform.

Part of a letter from [WSC] (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] in which he reports that he has begun to learn Greek verbs ending in "mi", describes a visit to the theatre with [Lady Wimborne, earlier Cornelia, Lady Guest and Lady Cornelia Churchill] and hints that he would like to be given an illustrated history of the American [civil] war as a birthday present.

Letter from "Winny" [WSC] ([29 & 30 Brunswick Road, Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] asking for money, books and autographs and saying that he hopes she is not intending to employ a tutor and "make my holiday miserable".

Letter from "Winny" [WSC] (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] in which he says that he is looking forward to his holidays and asks whether "Bertie" Roose may accompany him and requests books, autographs and money.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mama" [Lady Randolph Churchill] in which he says that he has read part of [Lord Randolph Churchill's] speech, reminds her to send him a copy of "She" and details his marks for conduct.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] in which he reminds her to send him a copy of "She" and says that he is contemplating writing a play to be performed at Christmas.

Letter from WSC (Bachelors' Club, Hamilton Place [London]) to "Mamma" [Lady Randolph Churchill] informing her that the War Office have given him permission to go to Cuba and that he has been instructed to collect information on the efficacy of a new bullet. He also says that he intends to buy Havana cigars and that he has discussed Cuba with Tito Holden.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] describing his journey and discussing arrangements to have his toy theatre sent to him.

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 Lord Randolph Churchill ([Rutland Cottage] Newmarket [Suffolk]) to [Lady Randolph Churchill] thanking her for her letters, describing the races at Newmarket, discussing the sale of a house and instructing her to take care of the baby [WSC].

Letter from Lord Randolph Churchill ([Rutland Cottage] Newmarket [Suffolk]) to [Lady Randolph Churchill] describing his success at the races and expressing his pleasure that the baby [WSC] is better.

Letter from Lord Randolph Churchill (Royal Station Hotel, York) to [Lady Randolph Churchill] in which he tells her that he is down o300 through losses at the races; discusses the possibility that Sir [?] Jatton may buy his racehorse the Abbesse for o3,000 and enclosing a bill [not present] for WSC.

Letter from Lord Randolph Churchill (Le Grand Hotel, Monte Carlo [Monaco]) to [Lady Randolph Churchill] in which he describes the leisurely way he spends his days and a visit to Nice [France]; speculates on the likelihood of a dissolution of Parliament and asks her to wish WSC a happy birthday on his behalf.

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 Lord Randolph Churchill (50 Grosvenor Square [London]) to [Lady Randolph Churchill] describing his journey and a hunting expedition with the Meath hounds and discussing his bedroom furniture. He adds that he has sent WSC a copy of his Sandhurst examination marks commenting that he should be pleased with his position of eighth despite criticism for impunctuality.

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 Lord Randolph Churchill (Moulton Paddocks, Newmarket [Suffolk]) to [Lady Randolph Churchill] describing a meeting with [Frances, Duchess of Marlborough] and Henry Fowler and his success at fishing. He says that he hopes to see her in London the following week, speculates on the success of various racehorses, and comments on a "capital letter" sent to him by WSC.

Letter from "Jack" [John S Churchill] (Versailles [France]) to "Mama" [Lady Randolph Churchill] in which he says that he is glad that WSC will miss the war in Greece as "he will not be able to agitate about it", describes a concert and his progress at the piano and asks her to send him money and musical scores.