Letter from [Dr] Robson Roose (29 & 30 Brunswick Road, Brighton [Hove, Sussex]) to Lord Randolph Churchill informing him that "we are still fighting the battle for your Boy [WSC]" and detailing WSC's condition.

Letter from Lord Randolph Churchill (Barton Lodge, Steeple-Aston, Oxfordshire) to [Lady Randolph Churchill] including: the trial for a case of attempted murder at Woodstock [Oxfordshire]; his intention to return to Ireland for Christmas; and his concern over WSC's health.

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 WSC (The Headmaster's, Harrow [School, Middlesex]) to "Jack" [John S Churchill] in which he asks whether Jack has settled down; informs him that he has a "dear little room" which he has decorated; discusses the possibility of visiting Jack and sending him stamps; and informs him that he has swapped 2 coins. Signed manuscript.

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 ([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 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 School, Middlesex]) to "Mama" [Lady Randolph Churchill] in which he apologises for not writing to her, reports that he has learnt 1,000 words of Macaulay and hopes that he will be awarded a "copy", a prize for English History.

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he describes the clothes he would like to wear when collecting a school prize and asks her to allow [Elizabeth] Everest to bring them to him and to help him pack.

Letter from WSC ([Harrow School, Middlesex]) to [Lady Randolph Churchill] thanking her for allowing "Jack" [John S Churchill] and [Elizabeth] Everest to visit him and asking her to visit him and bring him a hamper.

Letter from WSC ([Harrow School, Middlesex]) to "Papa" [Lord Randolph Churchill]in which he reports that he has secured his remove and that his form master is impressed with his progress, describes a mock battle and says that he intends to learn 1,000 lines of Shakespeare.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] reporting that he was not awarded the Shakespeare prize and apologising for not writing.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he says that he is glad that she has returned home and asks her to visit him.