Letter from WSC (The Headmaster's, Harrow [School, Middlesex]) to "Jack" [John S Churchill] in which he thanks him for some books and "P.O.O.'s" [Post Office Orders?]; says that he has purchased curtains for the den and instructs Jack to make 2 bunks for them to sleep in; and informs him that he has begun to study Chemistry. Signed manuscript. Typed transcript at CHAR 28/152A/3-4.

Transcript of a letter from WSC (The Headmaster's, Harrow [School, Middlesex]) to "Jack" [John S Churchill] in which he thanks him for some books and "P.O.O.'s" [Post Office Orders?]; says that he has purchased curtains for the den and instructs Jack to make 2 bunks for them to sleep in; and informs him that he has begun to study Chemistry. Typed. 2 copies. Original letter at CHAR 28/152A/2.

Letter from WSC (50 Grosvenor Square [London]) to "Jack" [John S Churchill] in which he promises to send photographs of [Lord Randolph Churchill and Lady Randolph Churchill]; recommends him to write home often as "papa only remembers getting one letter from you and a very unsatisfactory report"; and says that he has wasted 10 pounds "on a lot of old rubbish". Signed manuscript.

Letter from WSC (50 Grosvenor Square [London]) to "Jack" [John S Churchill] in which he describes a cash box which [Lady Randolph Churchill] has purchased for Jack; describes a walk with "Polly" [Adela] Hacket, a meeting with "Sunny" [Charles, 9th Duke of Marlborough] and luncheon with [Lady Randolph] at White's Club; and discusses rumours of [William] Gladstone's resignation. Signed manuscript. Typed transcript at CHAR 28/152A/21-22.

Transcript of a letter from WSC (50 Grosvenor Square [London]) to "Jack" [John S Churchill] in which he describes a cash box which [Lady Randolph Churchill] has purchased for Jack; describes a walk with "Polly" [Adela] Hacket, a meeting with "Sunny" [Charles, 9th Duke of Marlborough] and luncheon with [Lady Randolph] at White's Club; and discusses rumours of [William] Gladstone's resignation. Typed. 2 copies. Original letter at CHAR 28/152A/20.

Letter from WSC (50 Grosvenor Square [London]) to "Jack" [John S Churchill] including: thanks him for his long letter; his illness and the possibility that he may go to Brighton [Sussex]; news of various friends; a new Chemistry notebooks and an alteration in the period of history to be studied for the Sandhurst examination; and a promise to send money. Signed manuscript.

Letter from WSC (Royal Military College, Sandhurst [Camberley, Surrey]) to "Jack" [John S Churchill] in which he thanks him for his letter and discusses visiting Harrow at the weekend. Signed manuscript.

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 WSC (Royal Military College, Sandhurst [Camberley, Surrey]) to "Jack" [John S Churchill] thanking him for a present, discussing arrangements to visit Harrow, and informing him that [Lord Randolph Churchill and Lady Randolph Churchill] are returning [from Japan] to Monte Carlo as [Lord Randolph] has been advised to have "perfect quiet". Signed manuscript. Typed transcripts at CHAR 28/152A/32-33.

Transcript of a letter from WSC (Royal Military College, Sandhurst [Camberley, Surrey]) to "Jack" [John S Churchill] thanking him for a present, discussing arrangements to visit Harrow, and informing him that [Lord Randolph Churchill and Lady Randolph Churchill] are returning [from Japan] to Monte Carlo as [Lord Randolph] has been advised to have "perfect quiet". Typed. 2 copies. Original letter at CHAR 28/152A/31.

Letter from WSC (Royal Military College, Sandhurst [Camberley, Surrey]) to "Jack" [John S Churchill] informing him that [Lord Randolph Churchill and Lady Randolph Churchill] are returning [from Japan] to Monte Carlo and commenting on [Lord Randolph's] health "if he keeps perfectly quiet he may yet get well- though he will never be able to go into Politics." Signed manuscript. Typed transcripts at CHAR 28/152A/35-36.

Transcript of letter from WSC (Royal Military College, Sandhurst [Camberley, Surrey]) to "Jack" [John S Churchill] informing him that [Lord Randolph Churchill and Lady Randolph Churchill] are returning [from Japan] to Monte Carlo and commenting on [Lord Randolph's] health "if he keeps perfectly quiet he may yet get well- though he will never be able to go into Politics." Typed. 2 copies. Original letter at CHAR 28/152A/34.

Letter from [Lady Randolph Churchill] to [Lord Randolph Churchill] in which she discusses the pain of being separated from him, breakfast with [Henry] Standish and [Helene] Standish, reports compliments on her skating from Madame de Sagan and says that she is not lonely with "dear Winston"[WSC].

Part of a letter from [Lady Randolph Churchill] to [Lord Randolph Churchill] including: the announcement of the engagement of [Lady Rosamund Churchill, later Lady Fellowes and Lady De Ramsey to William Fellowes, later 2nd Lord De Ramsey]; a report in the Morning Post about his "remarks"; Lady Castlereagh's [later Lady Londonderry's] comments on the arguments between her family and the Marlboroughs; and WSC's progress.

Letter from [Lady Randolph Churchill] to [Lord Randolph Churchill] in which she discusses household accounts and the servants; asks about the Hague [The Netherlands] and [Lord] Blandford [later George, 8th Duke of Marlborough] and reports that WSC is missing him.

Letter from [Lady Randolph Churchill](Blenheim Palace) to [Lord Randolph Churchill] in which she discusses the sale of their house; comments on his family's disapproval of their plan to go abroad; reports that the baby [WSC] looks pale and that she feels "melancholy".

Letter from [Lady Randolph Churchill](Paris [France]) to [Lord Randolph Churchill] in which she gives instructions for [Elizabeth] Everest and the care of the baby [WSC]; expresses approval for his letter to [John, 7th] Duke [of Marlborough concerning Lord Blandford, later George, 8th Duke of Marlborough]; comments on the behaviour of [W H] Trafford; discusses financial affairs and the attachment between Clara [Jerome, later Clara Frewen] and Prince de Claremont.

Letter from [Frances, Duchess of Marlborough] (Branksome Dene, Bournemouth [Hampshire]) to [Lord] Randolph [Churchill] discussing arrangements for his return home and her poor health; asking whether he and Jennie [Lady Randolph Churchill] would like "Lily" [Lilian, Duchess of Marlborough, later Lady William Beresford] to care for [WSC and John S Churchill] and expressing a desire to see him.

Letter from [Frances, Duchess of Marlborough] (Grand Hotel, Scarborough [Yorkshire]) to [Lord] Randolph [Churchill] in which she says that she is unsure where to send letters to him; says that she thinks that "Jack" [John S Churchill] has enjoyed spending time with her; recommends that he should advise WSC about "diligence & hard work...economy & self denial" and expresses anxiety about his health.