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.

Letter from WSC (St George's School, Ascot [Berkshire]) to "Mamma" [Lady Randolph Churchill] thanking her for books and reporting that he has been to dinner with Lady Alfred Churchill.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he reproaches her for not replying to his last three letters, asks her to make a surgeon's appointment for him, and discusses his intention to sell his bicycle to buy "Dodo", a bull dog.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] informing her that he has won a cup for fencing, thanking her for oranges and reporting that he has to wear glasses.

Letter from WSC ([Harrow School, Middlesex]) to "Mama" [Lady Randolph Churchill] informing her that he is working hard at his fencing in which he represents the school, asks her to send his love to Lady [Laura] W[ilton] and to send him money to "replenish the exchequer".

Letter from WSC (St George's School, Ascot [Berkshire]) to [Lady Randolph Churchill] reporting that he has received a letter from "Jack" [John S Churchill] about which he comments "I think [Elizabeth] Everest held his hand" and that he has seen [Leonie Jerome, later Lady Leslie] and asking her to come to a concert.

Letter from WSC to "Mamma" [Lady Randolph Churchill] in which he says that he has nearly recovered from a cough and that he has had dinner with Lady Alfred Churchill.

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he informs her that he has moved into [James] Welldon's house, describes his room and various items he would like "Woom" [Elizabeth Everest] to send to him. Envelope present.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] informing her that he is "happy and quite well" and asking her to allow [Elizabeth] Everest to buy items for his room. Envelope present.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he informs her that he has joined the "Army class" and that he is learning French and geometrical drawing and studying for the Shakespeare prize. Envelope present.

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] asking her to allow [Elizabeth] Everest to send his bicycle for a "grand field day" at Wimbledon [Surrey] and to sign an order [?to permit him to fence]. Envelope present.

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] thanking her for sending him an order [?to permit him to fence] and asking her to visit him on Saturday. In a postscript he informs her that he has won a rifle shooting competition and includes a diagram of the position of his bullets. Includes envelope.

Photograph showing WSC as a toddler standing on a chair leaning against his mother. WSC has long curly hair and is wearing a velvet and lace dress, bead necklace and boots.

Portrait photograph showing John S Churchill and WSC, as young boys, leaning gently on Lady Randolph Churchill (centre).