Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] in which he reports that [Lord Randolph Churchill] has taken him to the Orleans Club.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] in which he apologises for not writing to her as he has been occupied with rehearsals and examinations and discusses arrangements for a Christmas party.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] in which he expresses his disappointment at not being able to spend his holidays with her and asks whether Mr Best may be able to teach him and "Jack" [John S Churchill].

Letter from WSC ([2 Connaught Place, London]) to [Lady Randolph Churchill] in which he reports that he has received school prizes for English and Scripture, describes Christmas day and an unwelcome invitation to Blenheim Palace from [Frances, Duchess of Marlborough] and says that "it is very dull without you".

Letter from WSC (45 Hill Street, Berkeley Square [London]) to [Lady Randolph Churchill] informing her that [Elizabeth] Everest is ill and that he and "Jack" [John S Churchill] are staying with Dr [Robson] Roose and feel "destitute".

Letter from WSC (46 Grosvenor Square [London]) to [Lady Randolph Churchill] in which he reports that he has been staying with [Frances, Duchess of Marlborough], that [Elizabeth] Everest has recovered and that he has been given a toy theatre. He discusses plans to see her during term time and a visit to the theatre to see "[HMS] Pinafore" The letter is dated to 1887, but internal evidence suggests that it dates to 1888.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Grandmama" [Frances, Duchess of Marlborough] informing her of his safe arrival and apologising for not writing previously.

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 ([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 WSC ([29 & 30 Brunswick Road, Hove, East Sussex]) to [Lady Randolph Churchill] in which he reports that he has nearly recovered and asks whether he may return to school late in order to see her during his holidays as "a week would make no difference to any one but you & me".

Letter from WSC to "Mamma" [Lady Randolph Churchill] in which he says that "Womany" [Elizabeth Everest] says that he is looking well that he is looking forward to seeing her and describes his symptoms.

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 (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] reporting that he has passed the entrance examination for Harrow School and describing the examination and a meeting with [James] Welldon. Envelope present.

Letter from WSC ([29 & 30 Brunswick Road, Hove, East Sussex]) to [Lady Randolph Churchill] in which he says that he has had mumps but hopes that he will be able to return home for easter.

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he says that he likes his school, that he has purchased a "frouster", asks her to send him food and money and says that he wishes to learn gymnastics. Envelope present.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] discussing arrangements to meet her and "Jack" [John S Churchill] and show them the school. Envelope present.

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.