Letter from Maggie Gooderidge, former servant of WSC's family, "better known as Maggie from Blenheim" (Chadderton Street, London W1) to WSC, with sympathy on his road accident in New York [United States] and a reminiscence about his childhood.

Letter from Louis Moriarty (Hillside, Harrow, [Middlesex]) to WSC congratulating him on his appointment as Under- Secretary of State for the Colonies and recalling his time as WSC's tutor.

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.

Drawing of WSC as a small child on a red sofa. Includes frame.

Letter from [Lady Randolph Churchill] (Belfast [Ulster, Ireland]) to "R" [Lord Randolph Churchill] in which she says that she has visited church twice and that she has been looking after the baby [WSC], that she hopes that [Lord] Blandford [later George, 8th Duke of Marlborough] will not mind him returning to her soon.

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].

Letter from [Lady Randolph Churchill]([Dublin, Ireland]) to [Lord Randolph Churchill] in which she describes the visitors she has received who include the Duke of Abercorn and [John, 7th Duke of Marlborough]; riding; invitations; the noise made by WSC and the running of the house with only one servant named Kate. Includes a cross marked "W [WSC] signature.

Letter from [Lady Randolph Churchill](Vice Regal Lodge, Dublin [Ireland]) to "R" [Lord Randolph Churchill] in which she says that she is bored, comments on a vulgar letter to [Lady] Rosamund [Churchill, later Lady Fellowes and Lady De Ramsey] and the date of Rosamund's wedding, and gives news of WSC.

Letter from [Lady Randolph Churchill] to "R" [Lord Randolph Churchill] in which she describes a morning with Mrs [Emelina] Guinness; reports on the purchase of a toy elephant for WSC; thanks him for buying her a saddle and complains of a cold.

Letter from [Lady Randolph Churchill] to "R" [Lord Randolph Churchill] in which she discusses riding and the progress of a horse, clothes for Thomas and a walk with WSC.

Part of a letter from [Lady Randolph Churchill] to [Lord Randolph Churchill] including: her loneliness; a conversation with "Annie" [Lady Bowmont, later Duchess of Roxburghe, earlier Lady Anne Churchill] who had said that she was "very much bored" at being pregnant; a visit to Dublin [Ireland] and a message from 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.

Part of a letter from [Lady Randolph Churchill] to [Lord Randolph Churchill] in which she says that she will inform people that [5th Lord] Rossmore [formerly Derrick Westenra] had called on her so that it would not appear that she was trying to hide it and reports that WSC is teething.