Letter from Lord Randolph Churchill (Government House, Bombay [India]) to [Lady Randolph Churchill] including: birthday greetings; comments on the "adventures" had by WSC; arguments between Leonie [Leslie, earlier Leonie Jerome] and the Leslie family; his opinion of Parsee practices; descriptions of his social engagements and those he has met, who included leading native politicians; his itinerary and a request that she should tell "Winnie" [WSC] that he has received his letter.

Letter from Lord Randolph Churchill (Residency Lucknow [India]) to [Lady Randolph Churchill] including: thanks for her letters and a request that she thank "little Winny" [WSC] for his letter which Lord Randolph describes as well written; his annoyance at a letter from [Sir Henry Drummond] Wolff; his poor opinion of the English in Lucknow; and observations on a meeting with the natives of Lucknow.

Letter from Lord Randolph Churchill (Hotel Bristol [5, Place Vendome, Paris, France]) to [Lady Randolph Churchill] including: description of his voyage; the names of those he has seen [in Paris], who included the Rothschilds; Henry James' opinion of an affidavit prepared by [Lord] Blandford [later George, 8th Duke of Marlborough] which is described as "vicious".

Letter from Lord Randolph Churchill (Bedford Hotel, Brighton [East Sussex]) to [Lady Randolph Churchill] expressing his distress that WSC's fever has returned, enclosing a telegram [not present] and including directions for [Dr Robson] Roose as to where he is staying.

Letter from Lord Randolph Churchill (Welbeck Abbey, Worksop [Nottinghamshire]) to [Lady Randolph Churchill] including the names of those present at the party and those he met at the races on the previous day and reports concerning [Lord] Blandford [later George, 8th Duke of Marlborough].

Letter from "Winny" [WSC] (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mama" [Lady Randolph Churchill] thanking her for her "epistle" and reporting that he has seen [Frances, Duchess of Marlborough].

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] informing her of his safe arrival, asking her not to let his bad behaviour influence his summer holidays and reporting that he has made good progress with Euclid.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lord Randolph Churchill] in which he expresses his pleasure that he is going to Harrow [School] rather than Winchester [School]; discusses his progress with Euclid, arithmetic and Greek; reports that he is to play roles in plays by Moliere and Aristophanes and says that he wished that his father could attend the distribution of prizes.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] in which he says that he would like her and [Lord Randolph Churchill] to attend the distribution of prizes, discusses his birthday party and the future examinations, and asks for more of her autographs as "there is rather a demand for them here".

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 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 (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 ([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 (The Head Master's, Harrow School [Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he expresses his disappointment that she did not come to visit him and asks her to visit him on the next day.

Letter from WSC (Reverend [James] Welldon's, Harrow School [Middlesex]) to "Papa" [Lord Randolph Churchill] discussing arrangements for speech day and the areas of the school which he could show his father.

Letter from WSC (Reverend [James] Welldon's, Harrow School [Middlesex]) to "Mamma" [Lady Randolph Churchill] asking her to persuade [Lord Randolph Churchill] to attend speech day and to allow [Elizabeth] Everest to visit him.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] reproaching her for forgetting him, asking her to send him money, to arrange an appointment with the oculist, and to sign a form permitting him to begin fencing.

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.

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he says that he enjoyed "Papa's" [Lord Randolph Churchill's] visit and that he is looking forward to the holidays. Envelope present.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he says that he had not worked hard due to laziness and consequently had received a bad report. He says that her letter "cut me up very much" and explains that he had replied to a letter from "Papa" [Lord Randolph Churchill] but that it had not been posted by the Page and describes his hopes of passing examinations in Geography, French and English dictation and composition. Envelope present.

Letter from WSC ([Banstead Manor, Newmarket, Suffolk]) to "Mamma" [Lady Randolph Churchill] informing her of his safe arrival, discussing activities he has planned and commenting that "Jack" [John S Churchill] sends her "14 pints of love and 26 brace of kisses". Envelope sealed with black wax.

Letter from WSC (Banstead Manor, Newmarket [Suffolk]) to "Mamma" [Lady Randolph Churchill] in which he says that he and "Jack" [John S Churchill] are enjoying themselves although he expresses his disappointment at not being allowed to shoot and describes [Lady Sarah Churchill, later Sarah Wilson] as being unpleasant towards him. Envelope present.