Letter from Lord Randolph Churchill (Novar, Evanton, Ross-shire [Ross and Cromarty, Scotland]) to [Lady Randolph Churchill] thanking her for her letters to him and requesting that she should thank WSC for his letter, approving of her decision to send "Jack" [John S Churchill] to Brighton [East Sussex] and predicting that [Sir] Charles Legard's letter [to the newspapers] will not harm him.

Letter from Lord Randolph Churchill (Banstead Manor, Newmarket [Suffolk]) to [Lady Randolph Churchill] reporting that [WSC and John S Churchill] have been good and that WSC rides well. He also relates his anger about arrangements for racing [his racehorse] Inverness and that WSC has made friends with the servants and is "full of local gossip".

Letter from Lord Randolph Churchill (Cliveden, Maidenhead [Buckinghamshire]) to [Lady Randolph Churchill] reporting his safe arrival at Cliveden; describing an evening spent at Moulton [Paddocks, Newmarket, Suffolk] where "Lady G" was amusing about her lovers and his success at the races at Windsor [Berkshire]; and commenting that [WSC and John S Churchill] are well and "permit us to lead a fairly tranquil existence".

Letter from Lord Randolph Churchill (Cliveden, Maidenhead [Buckinghamshire]) to [Lady Randolph Churchill] discussing financial matters and asking her to be more careful; describing an expedition to Oxford with [Lady] Sarah [Churchill, later Sarah Wilson], WSC and "Jack" [John S Churchill] and "Jack's" first ride on his pony and discussing arrangements for her to come to Cliveden.

Letter from Lord Randolph Churchill (Fort Salisbury [Rhodesia, later Harare, Zimbabwe]) to [Lady Randolph Churchill] in which he explains that he is waiting for [Cecil] Rhodes as he would like to discuss South African issues with him, speculates on British political affairs, and enquires about WSC's French lessons.

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.