Letter from Lord Randolph Churchill (Government House, Bombay [India]) to [Lady Randolph Churchill] including: birthday greetings; comments on the "adventures" had by WSC; arguments between Leonie [Leslie, earlier Leonie Jerome] and the Leslie family; his opinion of Parsee practices; descriptions of his social engagements and those he has met, who included leading native politicians; his itinerary and a request that she should tell "Winnie" [WSC] that he has received his letter.

Letter from Lord Randolph Churchill (Residency Lucknow [India]) to [Lady Randolph Churchill] including: thanks for her letters and a request that she thank "little Winny" [WSC] for his letter which Lord Randolph describes as well written; his annoyance at a letter from [Sir Henry Drummond] Wolff; his poor opinion of the English in Lucknow; and observations on a meeting with the natives of Lucknow.

Letter from Lord Randolph Churchill (Auchnashellach [Dingwall, Ross and Cromarty, Scotland] on the notepaper of the India Office) to [Lady Randolph Churchill] including sympathy for the difficulties experienced by Clara [Frewen, earlier Clara Jerome] in childbirth; a message for [Henry] Chaplin; his success at fishing; and the hope that she has provided some entertainment for "Winny" [WSC].

Letter from Lord Randolph Churchill (Makerstoun House, Kelso [Roxburghshire]) to Jennie [Lady Randolph Churchill] including: the success of a racehorse called Renard; the people he has met; comments on the British government's policy on Uganda and a visit to Harrow to see WSC and John S Churchill at which [James] Welldon had discussed the likelihood that WSC would pass his next examination.

Letter from Lord Randolph Churchill (50 Grosvenor Square [London]) to [Lady Randolph Churchill] describing his journey and a hunting expedition with the Meath hounds and discussing his bedroom furniture. He adds that he has sent WSC a copy of his Sandhurst examination marks commenting that he should be pleased with his position of eighth despite criticism for impunctuality.

Letter from Lord Randolph Churchill (Le Nid [Monte Carlo, Monaco]) to [Lady Randolph Churchill] describing a trip to Nice [France] and the people he has met who include "Ronny" [Ronald] Greville and attempts by the Duchess of Montrose to "take the Nid by storm". He also discusses WSC's riding expenses and asks her to draw WSC's attention to "expressions of authority".

Letter from WSC to "Mamma" [Lady Randolph Churchill] thanking her for presents of "soldiers, flags and castle" and sending her his love and "a great many kisses". Envelope present.

Letter from WSC ([Blenheim Palace]) to "Mamma" [Lady Randolph Churchill] in which he says that he is well and making progress with his lessons and that "Baby" [John S Churchill] is well.

Letter from WSC (Blenheim Palace) to "Papa" [Lord Randolph Churchill] in which he says that he hopes his father is getting better, that he has been picking primroses and that he has seen three "Indian children".

Letter from WSC (Blenheim Palace) to "Papa" [Lord Randolph Churchill] thanking him for his letter, and saying that he has been studying with [Frances, Duchess of Marlborough] who is going to London on the following day to see him and sending him and [Lady Randolph Churchill] "many kisses".

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 ([Blenheim Palace]) to "Papa" [Lord Randolph Churchill] in which he says that he has been to the Lince with "Baby" [John S Churchill] where he picked hyacinths, and that he has seen a snake which [Elizabeth] Everest would not let him kill.

Letter from WSC (2 Handborough Road, Ventnor [Isle of Wight]) to "Mamma" [Lady Randolph Churchill] thanking her for easter eggs and describing a picnic at Sandown where he saw "enormous 18 ton guns".

Letter from WSC to "Mamma" [Lady Randolph Churchill] asking her to visit him "I do want you to come down so much".

Letter from WSC (Blenheim Palace) to "Mamma" [Lady Randolph Churchill] in which he says that he is pleased to hear that [Lord Randolph Churchill] is better and describes riding in the park and seeing [John, 7th Duke of Marlborough].

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.