Letter from WSC (Harrow on the Hill [Middlesex]) to "Papa" [Lord Randolph Churchill] in which he says that he has been working hard for a good position in class, describes his activities with the army corps and reports that he is learning 1,000 lines of Macaulay for a prize and intends to try for the Shakespeare prize in the following term.

Letter from WSC ([Harrow School, Middlesex]) to [Lady Randolph Churchill] thanking her for allowing [Elizabeth] Everest and "Jack" [John S Churchill] to visit him and asking her to visit him. Envelope present.

Letter from WSC ([Harrow School, Middlesex]) to [Lady Randolph Churchill] detailing his reports for the previous week, expressing his hopes for future good reports and asking her not to be cross with him saying "I am not lazy & untidy but careless & forgetful". Envelope present.

Letter from WSC (Ventnor, Isle of Wight) to [Lady Randolph Churchill] describing his and "Jack's" [John S Churchill] enjoyment of their holiday with [Mary Balaam] sister of [Elizabeth Everest] "Woomany". Envelope present.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] apologising for not writing to her as he has been working for the Shakespeare prize and saying that he will not borrow money in future. Envelope present.

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] asking her to allow [Elizabeth] Everest to send his bicycle for a "grand field day" at Wimbledon [Surrey] and to sign an order [?to permit him to fence]. Envelope present.

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 (Harrow on the Hill [Middlesex]) to "Mama" [Lady Randolph Churchill] asking her to visit him as he would like her to "jaw" [James] Welldon about keeping him "on reports" and discussing arrangements for appointments with the doctor and dentist. In the hand of [James] Milbanke. Envelope present.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] informing her that he is "all right" although is suffering from a cough. Envelope present.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he expresses relief that "Grandpapa" [John, 7th Duke of Marlborough] has reached Brighton [East Sussex] and asks her to visit him as he has been "disappointed so many times about your coming". Envelope present.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mummy" [Lady Randolph Churchill] asking about the health of "Grandpapa" [John, 7th Duke of Marlborough] and requesting that [Elizabeth] Everest should make him an appointment with [Sir William] MacCormac as his leg is painful. Envelope present.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he says that [James] Welldon would like her to write to him to explain why WSC did not return to school until Thursday and asks her not to mention the theatre in her letter to Welldon.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mummy" [Lady Randolph Churchill] informing her that he has settled down well and that he has been permitted to study Chemistry instead of German and asking her to send him money.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] thanking her for sending him a speech by [Lord Randolph Churchill], anticipating that he will be placed near the top of the class in a recent ancient history examination and reporting that he has been placed top in algebra and history.

Letter from WSC ([2 Connaught Place, London]) to "Mamma" [Lady Randolph Churchill] thanking her for her "dis-ennuye-ing" letter, describing his illness and discussing the possibility that "Little Kim" [Lord Kimbolton later 9th Duke of Manchester] may have got lost.

Letter from WSC ([29 & 30 Brunswick Road, Hove, East Sussex]) to [Lady Randolph Churchill] informing her that his toy theatre has arrived safely and asking her to send him money.

Letter from Lord Randolph Churchill (Cliveden, Maidenhead [Buckinghamshire]) to [Lady Randolph Churchill] discussing financial matters and asking her to be more careful; describing an expedition to Oxford with [Lady] Sarah [Churchill, later Sarah Wilson], WSC and "Jack" [John S Churchill] and "Jack's" first ride on his pony and discussing arrangements for her to come to Cliveden.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Papa" [Lord Randolph Churchill] in which he says that he is getting on well and that "Mamma" [Lady Randolph Churchill] sent him some oranges from Monte Carlo [Monaco] and that he has received a letter from "Jack" [John S Churchill] about Elstree [Hertfordshire].

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] informing her that he has secured his remove and has started learning German and commenting on the success of the "Habbesse" [the Abbesse, one of Lord Randolph Churchill's racehorses].

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] discussing arrangements for her to visit him when she returns to England and requesting Latin dictionaries.

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 seeing her and [Lord Randolph Churchill], discusses the Harrow School entrance examination and his progress at school and requests dictionaries.

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 (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] discussing his prospects for the Harrow School entrance examination.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lord Randolph Churchill] discussing his prospects for the Harrow School entrance examination, detailing his progress with Virgil's Aeneid, Euclid, mathematics and other subjects and asking his father to visit him.

Letter from WSC (Harrow on the Hill [Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he details the form positions he expects in his examinations to secure his "Remove" and says that he hopes that [Lord Randolph Churchill] will visit for the "Cock House Match" [a football match]. Envelope present.