Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] in which he asks where [Lord Randolph Churchill] is and describes his financial situation and progress at swimming and with Euclid.

Letter from "Winny" [WSC] ([29 & 30 Brunswick Road, Hove, East Sussex]) to "Mama" [Lady Randolph Churchill] thanking her for a P[ostal] O[rder] and detailing his examination marks and positions. Envelope present.

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 ([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 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] 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] 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] 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 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.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mummy" [Lady Randolph Churchill] asking her to send him money.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he asks her to write [concerning James Welldon's proposal that WSC should spend part of his holidays in France] and to send him some money, and reports that he has been made a Lance Corporal.

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 (Harrow on the Hill [Middlesex]) to "Mummy" [Lady Randolph Churchill] asking her to send him money and informing her that he is going to see "Jack" [John S Churchill].

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] asking her to reimburse him for money spent on a visit to the doctor's and detailing what he has spent.

Letter from WSC (Harrow on the Hill [Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he explains that the money he had requested had been spent on journeys to [London] and defends his request to be sent ducks from Banstead [Manor, Newmarket, Suffolk] and asks her not to be "wrothful without cause".

Letter from WSC (Harrow on the Hill [Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he says that he has visited "Jack" [John S Churchill] and asks her to allow them to attend the wedding of [Lady] Sarah [Churchill, later Sarah Wilson to Gordon Wilson], not to send him to a French family for his holidays and to send him some "filthy lucre" [money].

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he says that he is "terrified" at the news that her purse has been stolen as he needs more money, bids her to invest her money in him rather than gambling and promises to send her a copy of the Harrovian containing a letter from him.

Letter from WSC (Hotel Couronne & Poste [?Brigue, Switzerland]) to "Mamma" [Lady Randolph Churchill] in which he says that he is looking forward to going to Sandhurst and that his French is impressive, objects to her comment that he has written "a scrap" [short letter] to "Grandmamma" [Frances, Duchess of Marlborough], expresses his determination to work hard at Sandhurst and asks her to suggest to [Lord Randolph Churchill] that he should be given an allowance.

Letter from WSC ([Harrow School, Middlesex] on the notepaper of Banstead Manor, Newmarket) to "Mamma" [Lady Randolph Churchill] in which he apologises that he has not had the time to write as he has been busy with the "assault at arms", informs her that he is depressed that the examinations have finished and encloses an account of his necessary end of term expenses. Envelope present which includes a note "Mind and come on Thursday and slang me and kiss me Mummy".