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 (50 Grosvenor Square [London]) to "Mamma" [Lady Randolph Churchill] asking her to persuade "Papa" [Lord Randolph Churchill] to give him an allowance and saying that he has been waiting for a letter from his father, who he hopes will be pleased that he [WSC] has got into the infantry at Sandhurst.

Letter from WSC ([Royal Military College, Sandhurst, Camberley, Surrey]) to "Mamma" [Lady Randolph Churchill] in which he explains that "Grandmamma" [Frances, Duchess of Marlborough] had not given him any money and that he had been forced to borrow some. He expresses his relief that "Papa" [Lord Randolph Churchill] is pleased that he [WSC] has got into the infantry.

Letter from WSC (50 Grosvenor Square [London]) to "Mamma" [Lady Randolph Churchill] in which he says that he does "the model 'son' very well", reports that he will probably accept an invitation from [Samuel, 2nd] Lord Hindlip, and that he and "Jack" [John S Churchill] miss her very much and discusses financial arrangements.

Letter from WSC (Royal Military College, Sandhurst, [Camberley, Surrey]) to "Mamma" [Lady Randolph Churchill] in which he discusses arrangements for a dentist's appointment and comments that "Papa" [Lord Randolph Churchill] has not sent him his allowance and that [Elizabeth] Everest has not received a cheque.

Letter from WSC (Royal Military College, Sandhurst, [Camberley, Surrey]) to "Mamma" [Lady Randolph Churchill] in which he reports that he is doing well and that he hopes that his examination results will please "Papa" [Lord Randolph Churchill], asks her to send him money and wishes her success with her concert.

Letter from WSC (Royal Military College, Sandhurst [Camberley, Surrey]) to "Mamma" [Lady Randolph Churchill] in which he thanks her for sending him a costume, discusses arrangements for her to visit him and asks her to send him money.

Letter from WSC (Hotel du Bar, Grindelwald [Switzerland]) to "Mamma" [Lady Randolph Churchill] describing his impressions of the scenery, reporting that he and "Jack" [John S Churchill] are being economical and that the rules for the Sandhurst entrance examination have been changed. He asks her to write and tell him how "Papa" [Lord Randolph Churchill] is and says that he is looking forward to her return.