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 ([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".

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] asking her to come and visit him and informing her that he does not have sufficient money to pay his subscriptions.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] asking for a postal order of 10 shillings, relating the success of the second run of the school play and discussing arrangements for his return (which include a maid being turned out of his room).

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] asking her to send him a postal order and discussing the start of examinations and arrangements for his return home.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] in which he reports that he has been unable to cash a postal order, describes an agricultural show and asks her to visit him.

Letter from "Winny" [WSC] (29 & 30 Brunswick Road [Hove, East Sussex]) to "Mama" [Lady Randolph Churchill] enclosing a photograph [not present] of himself and asking for money.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mama" [Lady Randolph Churchill] asking her whether she will allow him to learn the violincello instead of the piano, speculating on the Conservatives electoral prospects and asking for money as he is "bankrupt".

Letter from "Winny" [WSC] (Prospects House, Skegness [Lincolnshire]) to "Mamma" [Lady Randolph Churchill] apologising for not writing previously and asking for money. Annotated with a note in the hand of Elizabeth Everest that "Master Winston" is continually requesting money which he wastes and advising that he should not be given any more money. Envelope present.

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 ([Harrow School, Middlesex]) to [Lady Randolph Churchill] asking her to send him money.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he says that he does not need money, commenting "my Excheqeur is quite full at the moment" and asks her not to go to Mashonaland [Rhodesia, later Zimbabwe].