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.

Letter from WSC (Harrow on the Hill [Middlesex]) to "Mamma" [Lady Randolph Churchill] describing a lecture about the phonograph given by Colonel Gourand and asking whether he might be allowed to join the school workshop.

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.

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] asking her to send him money for subscriptions as "you promised I should not be different to others" and informing her of his position in class.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he describes his progress at school, (including in mathematics in which he is studying stocks), a "Sale by Auction" and a paper chase and says that he hopes she is enjoying her "spree on the continong [continent]".

Letter from WSC ([Harrow School, Middlesex]) to "Papa" [Lord Randolph Churchill] asking him to write to [James] Welldon concerning his school house and describing a "sham fight" with other schools.

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 "Papa" [Lord Randolph Churchill] informing his father that he has secured his remove.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mama" [Lady Randolph Churchill] informing her that he has secured his remove and thanking her for sending him oranges.

Letter from "Winny" [WSC] (The Head Master's, Harrow School [Middlesex]) to "Woom" [Elizabeth Everest] informing her of his safe arrival and detailing the clothes he has ordered.

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 "Winny" [WSC] ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he explains that he has been working very hard and details his hopes for success in individual subjects and comments that he is "afraid some enemy hath sown tares in your mind".

Letter from WSC ([Banstead Manor, Newmarket, Suffolk]) to "Mummy" [Lady Randolph Churchill] describing the number of rabbits he has "slaughtered" and the cold weather.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he says that he is sorry that she could not visit him, asks her to allow [Elizabeth] Everest to bring him ornaments, details the "'oof'" [money] he has spent on furnishing his room and money which he owes, and asks her to send him a P[ost] O[ffice] O[rder] and to ask [James] Welldon to allow him to visit [John, 7th Duke of Marlborough].