Letter from Lord Randolph Churchill, Hotel del Monte, California, to WSC, on WSC's desire to join the cavalry rather than the 60th Rifles, pointing out that the Duke of Cambridge would be extremely angry, and that he would also oppose the change strongly, also on Lord and Lady Randolph's visit to the United States, and forthcoming Voyage to Japan.

Letter from WSC [letter signed "De Profundis"] to "The Harrovian" on the inadequacy of certain classrooms at Harrow School, recommending that new classrooms be built [copy].

Letter from Frances, Duchess of Marlborough, Ramsey Abbey Huntingdon, to WSC, congratulations on obtaining Infantry Cadetship, also on the progress of the Home Rule Bill in the House of Lords.

Letter from Lady Randolph Churchill, Sunningdale, to WSC, on her visit to the Ascot races, and on the Sandhurst entrance examination.

Letter from Lady Randolph Churchill, Kissingen, to WSC, on his success in the Sandhurst entrance examination, and his father's anger that he failed to obtain an Infantry cadetship, also on her visit to Germany and meeting with Bismarck.

Letter from Lady Randolph Churchill, 50 Grosvenor Square, London, to WSC, on his visit to the 4th Hussars at Aldershot "I am not sure if Papa would approve".

WSC's history notebook, [from ?Harrow School] containing notes on: The War of the Spanish Succession, with accounts and maps of the First Duke of Marlborough's campaigns, The Literature of Queen Anne's Reign, The Darien Scheme, Scotch Affairs, 1702-1714, The Fortunes of Parties, 1702-1714, The Reign of George I, The Reign of George II.

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 (The Head Master's, Harrow School [Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he says that he is getting on well and will sit his preliminary examination for Sandhurst in June, and asks to be allowed to do additional drawing classes and to continue fencing.

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 Lord Randolph Churchill (Fort Salisbury [Rhodesia]) 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.

School report for WSC from St George's School, Ascot [Berkshire] giving his place in his form, the number of times he was late and comments from his teachers on his progress in various subjects. Includes a note that WSC is "a regular 'pickle' in many ways.".

School report for WSC from St George's School, Ascot [Berkshire] giving his place in his form, the number of times he was late and comments from his teachers on his progress in various subjects.

School report for WSC from St George's School, Ascot [Berkshire] giving his place in his form, the number of times he was late and comments from his teachers on his progress in various subjects. Includes a comment that WSC "Does not quite understand the meaning of hard work".

School report for WSC from St George's School, Ascot [Berkshire] giving his place in his form, the number of times he was late and comments from his teachers on his progress in various subjects.

School report for WSC from St George's School, Ascot [Berkshire] giving his place in his form, the number of times he was late and comments from his teachers on his progress in various subjects. Includes a comment that WSC "is rather greedy at meals".

School report for WSC from St George's School, Ascot [Berkshire] giving his place in his form, the number of times he was late and comments from his teachers on his progress in various subjects.

School report for WSC from St George's School, Ascot [Berkshire] giving his place in his form, the number of times he was late and comments from his teachers on his progress in various subjects. Includes a comment that WSC "has no ambition - if he were really to exert himself he might yet be 1st at the end.".

School report for WSC from his school at 29 & 30 Brunswick Road [Hove, Sussex] giving his marks and form positions for various subjects and comments from Miss C Thomson on his improvement .

School report for WSC from his school at 29 & 30 Brunswick Road [Hove, Sussex] giving his marks and form positions for various subjects and comments from [Miss C Thomson] on his satisfactory progress .

School report for WSC from his school at 29 & 30 Brunswick Road [Hove, Sussex] giving his marks and form positions for various subjects and comments from [Miss C Thomson] on his "very marked" progress and her hopes that he will do well .