Letter from WSC (Royal Military College, Sandhurst [Camberley, Surrey]) to "Jack" [John S Churchill] in which he thanks him for his letter; reports that he has visited the 4th Hussars at Aldershot [Surrey] with Colonel [John] Brabazon; discusses "the watch" [WSC had ill treated a gold watch] and reports that "Papa [Lord Randolph Churchill] is now soothed"; discusses their summer holiday and their next meeting; and reports that the typewriter has arrived. Signed manuscript.

Letter from WSC (Royal Military College, Sandhurst [Camberley, Surrey]) to "Jack" [John S Churchill] including: a visit to the Empire [theatre, London]; his intention to bring "Molly" [Adela] Hacket to Harrow; a planned visit to the Derby if [Lord Randolph Churchill] gives his permission; and his progress with a typewriter. Typescript signed by WSC.

Letter from WSC (Royal Military College, Sandhurst [Camberley, Surrey]) to "Jack" [John S Churchill] including: a visit to the races at Ascot [Surrey] and dinner with Lord Wolverton; his hopes to see Jack; and the comment "Everything is very damneble [sic] except Sandhurst". Typescript signed by WSC.

Letter from "Jack" [John] S Churchill (Andermatt [Switzerland) to "Mama" [Lady Randolph Churchill] describing his journey and climbing Pilatus. He also reports that "Winney" [WSC] "went nearly mad" at the news that he had passed the Sandhurst examination and is writing to "Papa" [Lord Randolph Churchill].

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he expresses pleasure that he is not going abroad for his holidays, describes arrangements for a camp and asks her to give him money and to buy him a pair of butcher boots. He encloses the camp regulations [not present] and suggests that she might approach officers at Aldershot [Hampshire] to introduce themselves to him.

Letter from WSC (The Hatch) to "Mamma" [Lady Randolph Churchill] describing a week he spent in London and his social engagements, a visit to the races at Sandown [Surrey] and to Harrow with "Molly" [Adela] Hacket and discussing his planned itinerary for a visit to Switzerland. He comments that he hopes that "Papa" [Lord Randolph Churchill] will not be angry that he would like to join the cavalry.

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 WSC (Royal Military College, Sandhurst [Camberley, Surrey]) to "Mamma" [Lady Randolph Churchill] in which he discusses his hope to return home at the weekend, commenting "I can't endure two Sundays running at this place" and describing his plans to visit the Empire [theatre, London].

Letter from WSC (Bangalore [India]) to "Mamma" [Lady Randolph Churchill] including: his injury while playing polo; a list of the books he has read while in India; his method of constructing "a scaffolding of logical and consistent views" through studying the Annual Register; observations on education; and arrangements for caring for "Firefly" [a horse] which he is sending to England.

Letter from WSC (Hotel Couronne & Poste [?Brigue, Switzerland]) to "Mamma" [Lady Randolph Churchill] in which he says that he is looking forward to going to Sandhurst and that his French is impressive, objects to her comment that he has written "a scrap" [short letter] to "Grandmamma" [Frances, Duchess of Marlborough], expresses his determination to work hard at Sandhurst and asks her to suggest to [Lord Randolph Churchill] that he should be given an allowance.

Letter from WSC (50 Grosvenor Square [London]) to "Mamma" [Lady Randolph Churchill] asking her to persuade "Papa" [Lord Randolph Churchill] to give him an allowance and saying that he has been waiting for a letter from his father, who he hopes will be pleased that he [WSC] has got into the infantry at Sandhurst.

Letter from WSC ([Royal Military College, Sandhurst, Camberley, Surrey]) to "Mamma" [Lady Randolph Churchill] in which he explains that "Grandmamma" [Frances, Duchess of Marlborough] had not given him any money and that he had been forced to borrow some. He expresses his relief that "Papa" [Lord Randolph Churchill] is pleased that he [WSC] has got into the infantry.

Letter from WSC ([Royal Military College, Sandhurst, Camberley, Surrey] on the notepaper of 15 Grosvenor Square) to "Mamma" [Lady Randolph Churchill] in which he says that her letter had made him unhappy and explains that he makes a considerable effort over his letters to "Papa" [Lord Randolph Churchill]. He also discusses his father's refusal to grant him permission to play polo, describes an accident suffered by his riding companion and comments on his own physical feebleness.

Letter from WSC (Hotel Continental, Milan [Italy]) to "Mama" [Lady Randolph Churchill] in which he expresses his disappointment at [Lord Randolph Churchill's] displeasure with him over his results in the [entrance] examination [for Sandhurst] after his hard work. He discusses his marks in individual subjects and says that he has a chance to alter his father's opinion of him.

Letter from "Jack" [John] S Churchill (Harrow on the Hill [Middlesex]) to "Mama" [Lady Randolph Churchill] in which he reports that "Winney" [WSC] appears to be enjoying Sandhurst despite a boil on his face and seems to have grown two inches. He also says that a Constitutional Club is to be opened the following week.

Letter from "Jack" [John] S Churchill (The Deepdene, Dorking [Surrey]) to "Papa" [Lord Randolph Churchill] in which he says that he is staying with Aunt Lily [Lady William Beresford] who is ill, reports that WSC has "come out second" in the riding at Sandhurst and remarks that he is expecting a telegram to hear that he (Lord Randolph) has arrived at Marseilles [France].

Letter from "Jack" [John] S Churchill (Harrow [School, Middlesex]) to "Papa" [Lord Randolph Churchill] including: his intention to stay with "Grandmama" [Frances, Duchess of Marlborough] and WSC at Branksome Dene; his intention to be confirmed the following year and WSC's progress at Sandhurst.

Contains accounts and maps of the First Duke of Marlborough's campaigns and general notes on eighteenth and nineteenth century history.