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 Laura, Lady Wilton (later Lady Johnstone), Le Nid, Monte Carlo, to WSC, on the Sandhurst Entrance Examination.

Letter from John Milbanke, Depot, Royal Sussex Regiment, to WSC, on WSC's life at Harrow School, and success in the Army Preliminary Examination, and Milbanke's life in the Royal Sussex Regiment.

Letter from Charlotte Thomson to WSC, on Brunswick Road School, Brighton.

Letter from Maxwell McTaggart to WSC, on the Sandhurst Entrance Examination.

Letter from Louis Moriarty, Army Class Master, Harrow School, to WSC, on WSC's "very creditable" failure in the Sandhurst entrance examination. Stating that if he worked "earnestly and sensibly" he would pass in November.

Letter from Rev. James Welldon, Headmaster, Harrow School, to WSC, on his failure in the Sandhurst entrance examination. Urging him to work "not by fits and starts but with regular persistent industry". Commenting that the grammatical foundation of his language was so uncertain that he lost marks which other boys gained "You therefore have ground to make up as well as new ground to cover".

Letter from Louis Moriarty, Army Class Master, Harrow School, to WSC, listing the numbers of the Harrow candidates in the Sandhurst entrance examination.

Letter from Colonel John Brabazon to WSC, invitation to visit 4th Hussars at Aldershot, and to meet Captain Julian Byng, 10th Hussars [later Lord Byng of Vimy].

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 [Lady Randolph Churchill](2 Connaught Place [London]) to [Lord Randolph Churchill] including: an invitation from Lady [Laura] Wilton; concern about the health of "Papa" [Leonard Jerome]; observations about Norah Stirling; the opinions of Lord Hartington [later 8th Duke of Devonshire] about [Charles] Parnell; political affairs; an interview with [James] Welldon about WSC and discussion of a new coachman.

Letter from [Lady Randolph Churchill](2 Connaught Place [London]) to [Lord Randolph Churchill] including: her decision not to go to Monte Carlo [Monaco]; the deterioration in the health of "Papa" [Leonard Jerome]; the illness of [Frances, Duchess of Marlborough]; and news that WSC has passed his Preliminary Examination in all subjects and is in a special Sandhurst class, an achievement for which she suggests he should be rewarded.

Letter from [Lady Randolph Churchill](2 Connaught Place [London]) to [Lord Randolph Churchill] including: political news about [Charles] Parnell and the Irish from [Lord] Hartington [later 8th Duke of Devonshire]; her irritation that [Frances, Duchess of Marlborough] has asked her to take [Lady] Sarah [Churchill, later Sarah Wilson] to the theatre; and WSC's improvement at school.

Letter from Lord Randolph Churchill (Fort Salisbury [Rhodesia, later Harare, Zimbabwe]) 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.