Letter from WSC (45 Hill Street, Berkeley Square [London]) to [Lady Randolph Churchill] informing her that [Elizabeth] Everest is ill and that he and "Jack" [John S Churchill] are staying with Dr [Robson] Roose and feel "destitute".

Letter from WSC (46 Grosvenor Square [London]) to [Lady Randolph Churchill] in which he reports that he has been staying with [Frances, Duchess of Marlborough], that [Elizabeth] Everest has recovered and that he has been given a toy theatre. He discusses plans to see her during term time and a visit to the theatre to see "[HMS] Pinafore" The letter is dated to 1887, but internal evidence suggests that it dates to 1888.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Grandmama" [Frances, Duchess of Marlborough] informing her of his safe arrival and apologising for not writing previously.

Letter from WSC ([Harrow School, Middlesex]) to "Mama" [Lady Randolph Churchill] in which he apologises for not writing to her, reports that he has learnt 1,000 words of Macaulay and hopes that he will be awarded a "copy", a prize for English History.

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he describes the clothes he would like to wear when collecting a school prize and asks her to allow [Elizabeth] Everest to bring them to him and to help him pack.

Letter from WSC ([Harrow School, Middlesex]) to [Lady Randolph Churchill] thanking her for allowing "Jack" [John S Churchill] and [Elizabeth] Everest to visit him and asking her to visit him and bring him a hamper.

Letter from WSC ([Harrow School, Middlesex]) to [Lady Randolph Churchill] expressing his pleasure that she is coming to visit him and promising her that he will be "specially got up for the occasion".

Letter from WSC ([Harrow School, Middlesex]) to "Papa" [Lord Randolph Churchill]in which he reports that he has secured his remove and that his form master is impressed with his progress, describes a mock battle and says that he intends to learn 1,000 lines of Shakespeare.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] reporting that he was not awarded the Shakespeare prize and apologising for not writing.

Letter from WSC ([2 Connaught Place, London]) to "Mamma" [Lady Randolph Churchill] thanking her for her "dis-ennuye-ing" letter, describing his illness and discussing the possibility that "Little Kim" [Lord Kimbolton later 9th Duke of Manchester] may have got lost.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he says that he is glad that she has returned home and asks her to visit him.

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he says that he feels weak and ill and asks her to allow "Woomany" [Elizabeth Everest] to visit him.

Letter from WSC ([Harrow School, Middlesex]) to "Mama" [Lady Randolph Churchill] thanking her for allowing "Woomany" [Elizabeth Everest] to visit him and asking her to allow her to continue to visit him.

Letter from WSC ([Harrow School, Middlesex]) to "Papa" [Lord Randolph Churchill] thanking him for the money to buy a bicycle and apologising for not writing sooner.

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he says that he is enjoying being in [James] Welldon's house and asks her to send him money and to visit him.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he says that he is well and describes his success at a rifle range.

Letter from WSC ([Harrow School, Middlesex]) to "Mama" [Lady Randolph Churchill] in which he reports that he has fallen on the back of his head and asks her to come and visit him.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] thanking her for allowing "Woom" [Elizabeth Everest] to visit him although he says that he was disappointed at not seeing her [Lady Randolph] and asks her to visit him.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] thanking her for allowing "Woom" [Elizabeth Everest] visit him and saying that the doctor has advised him that he should rest and that he would like to come home.

Letter from "Winny" [WSC] ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he describes his bicycle accident, asks her to visit him and to allow [Elizabeth] Everest to visit as he is bored.

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

Letter from "Winny" [WSC] ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] describing the extent of an outbreak of measles at school and asking her to allow him to return home, commenting "I should have imagined that as 300 mamas & 300 papas like to have their 'offsprings' home you would like to have me".

Letter from WSC to "Mamma" [Lady Randolph Churchill] informing her that he and "Jack" [John S Churchill] have arrived safely and that "Jack" felt tired and attributed it to a fishbone which he had swallowed six months previously and describing a visit to a landslip.

Card from WSC (Harrow on the Hill [Middlesex]) to "Mama" [Lady Randolph Churchill] informing her of his safe arrival and that he is sharing a room with Count Eric Steenbock [Stenbock, the son of a Swedish-Norwegian Minister] and is not spending his money rashly.

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].