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].

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he expresses relief about the health of [John, 7th Duke of Marlborough], says that he is looking forward to seeing [Lord Randolph Churchill] and advises her not to make herself ill with worry.

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] complaining of toothache and informing her that he has secured his remove and become "Head of the Fags".

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mummy" [Lady Randolph Churchill] complaining of toothache and requesting that she should send him money to travel to an appointment with the dentist as he has paid his debts and given up betting.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] informing her that his toothache has gone, asking after "poor Grandmamma Duchess" [Frances, Duchess of Marlborough] and requesting that she should send him money for subscriptions Annotated "Hurrah for Nunthorpe" [a racehorse which had won the Great Jubilee Stakes at Kempton Park races].

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] informing her that he has been in the "deuce of a row" for breaking factory windows and asking her to send him money as he is "absolutely 'oofless'".

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mummy"[Lady Randolph Churchill] in which he informs her that his [toothache] has got better, asks about the health of various animals and says that [Elizabeth] Everest has sent him a hamper.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he informs her that he has had his tooth taken out and asks her to send him money.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] asking her to meet him and to send him money to pay a "bicycle debt" and to repair [factory] windows which he had smashed.