Cuttings of the following articles by WSC from "My Life": "Taken Prisoner by the Boers" on WSC as a war correspondent in South Africa; "My Escape from Pretoria"; "My Entry into Politics" on writing Lord Randolph Churchill's autobiography and the Free Trade issue; "Changing the Political Camp" on going over to the Liberals, South Africa and the Board of Trade; Looking Back on Sixty Years" on WSC's childhood, education and time at Sandhurst.

Letters from Elizabeth Everest [Churchill family Nanny] to WSC and John S Churchill.

Letter from Lady Randolph Churchill, 2 Connaught Place, London, to WSC, on his "very bad" school report from Harrow Describing his work as an "insult to his intelligence", and contrasting him to his brother Jack "who comes out at the head of his class every week".

Letter from Jack Milbanke (17 Cliveden Place, Eaton Square) to WSC, offering help, and to intercede with Lady Randolph Churchill if he could be of any use.

Letter from "Jack" John S Churchill (Banstead Manor, Newmarket) to WSC, on their "den" which was dirty inside, but had withstood the weather well, and on the health of the animals.

Letter from "Jack" [John S Churchill] (Elstree School, Herts) to WSC, on the Harrow Fencing Cup.

Letter from "Jack" [John S Churchill] (Harrow School) to WSC, With little to report due to WSC's recent visit, commenting on WSC's good time in London.

Letter from Lord Randolph Churchill, 2 Connaught Place, London to WSC, thanks for letters containing news of Harrow, also commenting on the death of "poor Daisy" and sending postal order for 21s.

Letter from Lord Randolph Churchill, 2 Connaught Place, London to WSC, on the need for WSC to return to Harrow a week early to prepare for the Sandhurst entrance examination, with Lord Randolph's reminiscences about his final examinations at Oxford. Also commenting on the death of the Duke of Clarence "one Of the saddest events I have ever known".

Part of a letter from [Lady Randolph Churchill] (2 Connaught Place [London]) to [Lord Randolph Churchill] including: a sea crossing in the Calabria and her illness; the possibility that "Mama" [Clara Jerome] may go to the United States and that Clara [Frewen, earlier Clara Jerome] might be alone; a suggestion that he should avoid writing "melancholy" letters to [Frances, Duchess of Marlborough]; progress with the decoration of a studio; and news of "Jack" [John S Churchill] and WSC.

Letter from WSC (Brighton [Sussex]) to "Papa" [Lady Randolph Churchill] in which he says that he hopes his father had a good journey [to India] and that he watched his father's ship sailing away.

Letter from [Lady Randolph Churchill] to [Lord Randolph Churchill] in which she describes an evening with the de Mondys, reports that the baby [WSC] is better but sad that he is away and asks him to send her regards to [Lord] Blandford [later George, 8th Duke of Marlborough].

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.