Letter from Lord Randolph Churchill (Villa Carmen, Monte Carlo [Monaco]) to [Lady Randolph Churchill] including: his apologies for forgetting her birthday; arrangements for her journey to Monte Carlo; Annie's position [Duchess of Roxburghe, earlier Lady Anne Churchill and Lady Bowmont] as Mistress of the Robes; observations on the dullness of letters from [Sir Henry Drummond] Wolff; and a request that she should give WSC some money before he returns to school.

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 ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he discusses purchasing a bull dog, asks her to make a doctor's appointment for him and to write to [James] Welldon to thank him for arranging private lessons for him.

Letter from WSC (Harrow on the Hill [Middlesex]) to "Mummy" [Lady Randolph Churchill] asking her to send him money and informing her that he is going to see "Jack" [John S Churchill].

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] asking her to reimburse him for money spent on a visit to the doctor's and detailing what he has spent.

Letter from WSC (Harrow on the Hill [Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he explains that the money he had requested had been spent on journeys to [London] and defends his request to be sent ducks from Banstead [Manor, Newmarket, Suffolk] and asks her not to be "wrothful without cause".

Letter from WSC (Harrow on the Hill [Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he says that he has visited "Jack" [John S Churchill] and asks her to allow them to attend the wedding of [Lady] Sarah [Churchill, later Sarah Wilson to Gordon Wilson], not to send him to a French family for his holidays and to send him some "filthy lucre" [money].

Letter from WSC (Harrow on the Hill [Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he thanks her for sending him money, asks her to allow him to attend the wedding of [Lady Sarah Churchill, later Sarah Wilson to Gordon Wilson] and begs her not to make him spend his holidays with a "nasty, fusty and beastly" French family.

Letter from WSC (Harrow on the Hill [Middlesex]) to "Mamma" [Lady Randolph Churchill] informing her of his safe return, asking her to allow [Elizabeth] Everest and "Jack" [John S Churchill] to visit him, and commenting on his bad luck in being obliged to leave [the wedding of Lady Sarah Churchill, later Sarah Wilson to Gordon Wilson] when he was "making an impression on the pretty Miss Weaslet".

Letter from WSC (Harrow on the Hill [Middlesex]) to "Mamma" [Lady Randolph Churchill] asking her not to send him to Paris [France] before Christmas warning her that if she does "the holidays will be one continual battle".

Letter from WSC (Harrow on the Hill [Middlesex]) to "Mamma" [Lady Randolph Churchill] concerning the possibility that she might send him to Paris [France] before Christmas, asking her to consider his happiness "There are other and higher things in this world than learning, more powerful agents than the Civil Service Commissioners".

Letter from WSC (Harrow on the Hill [Middlesex]) to "Mummy" [Lady Randolph Churchill] concerning the possibility that she might send him to Paris [France] before Christmas. He asks her to write to [James] Welldon concerning the date he may return home commenting "Welldon; he is the cause of all my misfortunes" and on arrangements made with Baron [Moritz] H[irsch] "I expect this little French brute will spoil it all".