Letter from WSC ("In the train near East London", South Africa]) to "Mamma" [Lady Randolph Churchill] informing her that he is travelling to Natal with Captain [Alexander] Campbell and [John] Atkins from the Manchester Guardian. He observes that the Boer forces have been underestimated and that there will be "a fierce and bloody struggle" and expresses his hope that he is ahead of other newspaper correspondents.

Letter from John S Churchill (Elstree School, Hertfordshire) to "Mama" [Lady Randolph Churchill] in which he says that "Winny" [WSC] was not allowed to visit him as he had broken a window, reports on his position in his form and says that he is looking forward to returning home for [cricket at] Lords.

Letter from [John S Churchill] (Elstree School [Hertfordshire]) to "Mama" [Lady Randolph Churchill] describing a visit from "Winney" [WSC] and asking about her plans for the holiday, commenting "Do let me keep with Winney whatever happens".

Letter from "Jack" [John] S Churchill (Elstree School, Hertfordshire) to "Mama" [Lady Randolph Churchill] in which he asks her to allow him to see "Winney" [WSC] during the holiday and to write to him.

Letter from "Jack" [John] S Churchill (Elstree School, Hertfordshire) to "Mama" [Lady Randolph Churchill] in which he asks her whether "Winney" [WSC] will have to go to France during the holidays; asks her to let him see him and to send him some money; and discusses arrangements for his return home.

Letter from "Jack" [John] S Churchill (Elstree School, Hertfordshire) to "Mama" [Lady Randolph Churchill] in which he describes a fit experienced by Mr Sanderson, one of his schoolmasters, says that he has not heard from "Winney" [WSC] and that "Papa" [Lord Randolph Churchill] is too busy to visit him. Also numbered "70".

Letter from "Jack" [John] S Churchill ([Harrow School, Middlesex]) to "Papa" [Lord Randolph Churchill] in which he says that "Winney" [WSC] is looking after him, discusses arrangements to have his watch sent to Dent's and says that he prefers [Harrow] to Elstree [his previous school].

Letter from "Jack" [John] S Churchill ([Harrow School, Middlesex]) to "Mama" [Lady Randolph Churchill] in which he says that "Winney" [WSC] is looking after him, that he has passed the arithmetic exam and that he has been given a nice room.

Letter from WSC (Blenheim Palace) to "Mama" [Lady Randolph Churchill] in which he says that he has been for a drive and that he is greatly enjoying being in the country where he has been making "encampments", and sends his and [John S Churchill's] love to her and to "Papa" [Lord Randolph Churchill].

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].

Part of a letter from WSC ([Harrow School, Middlesex]) to [Lady Randolph Churchill] asking her to come and speak to [James] Welldon and "stick up for" him.

Letter from WSC (Blenheim Palace) to "Mama" [Lady Randolph Churchill] asking her to come to Blenheim again and describing riding the pony Rob Roy.

Letter from WSC (Beech Lodge [Wimbledon, Surrey]) to "Papa" [Lord Randolph Churchill] thanking him for his letter, expressing relief that [Lord Randolph] is better and sending love to [sic] "Sunney" [later Charles, 9th Duke of Marlborough].

Letter from WSC (St George's School [Ascot, Berkshire]) to "Papa" [Lord Randolph Churchill] in which he says that he is "very happy" at school, that he has been given a bracket by Mrs Kynnersley and that he intends to send his father a gazette.

Letter from WSC (St George's School [Ascot, Berkshire]) to "Mamma" [Lady Randolph Churchill] in which he says that he is "very happy" at school and has spent a happy birthday, thanks her for a present and asks her not to forget to visit him.

Letter from WSC [(St George's School, Ascot, Berkshire]) to "Mamma" [Lady Randolph Churchill] in which he asks her whether he will see [Elizabeth] Everest during the holidays.

Letter from WSC (St George's School, Ascot [Berkshire]) to "Mamma" [Lady Randolph Churchill] in which he says that he hopes that she will visit him soon, asks whether [Elizabeth] Everest gave her the "flour" from him and calculates that he will return home in a month's time.

Letter from WSC (St George's School, Ascot [Berkshire]) to "Mama" [Lady Randolph Churchill] in which he says that he hopes that she will visit him and will allow [Elizabeth] Everest and "Jack" [John S Churchill] to come and see the athletics. Contains pencil guest lists in the hand of ?Lady Randolph Churchill.

Letter from [WSC] (St George's School, Ascot [Berkshire]) to "Oom" [Elizabeth ] saying that he will see her on the 31st of the month.

Letter from [WSC] to "Mamma" [Lady Randolph Churchill] in which he relates that he has caught his first fish and that he and "Jack" [John S Churchill] are well.

Letter from WSC (St George's School, Ascot [Berkshire]) to "Mama" [Lady Randolph Churchill] thanking her for sending him a bag, apologising for not sending it "oweing to my lazyness" and sending regards to [Clara Frewen, earlier Clara Jerome and Leonie Jerome, later Leonie Leslie].

Letter from WSC (St George's School, Ascot [Berkshire]) to "Mamma" [Lady Randolph Churchill] describing a visit to Hampton Court [Middlesex].

Letter from WSC (St George's School, Ascot [Berkshire]) to "Mama" [Lady Randolph Churchill] discussing a firework party at which there will be two guys [Charles] Bradlaugh and O'Donovan Rossa [Jeremiah O'Donovan] and giving the names of the songs he sings in the singing class.