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".

Telegram from Lord Randolph Churchill to WSC, confirming that he had forwarded Sandhurst papers and a cheque to WSC.

Letter from Lord Randolph Churchill, Le Nid, Monte Carlo, Monaco, to WSC, urging him to work hard at Sandhurst - to "keep the standard up & keep raising"...Pull yourself together & keep yourself well abreast & even ahead of those you are competing with..Keep down the smoking, keep down the drink & go to bed as early as you can" With postscript suggesting that he should substitute "father" for "papa" in future letters.

Letter from Lord Randolph Churchill, 50 Grosvenor Square, London, to WSC, complaining about WSC's frequent visits to London from Sandhurst, forbidding him to come to London more than once a month, and encouraging him to study at weekends.

Letter from Lord Randolph Churchill, 50 Grosvenor Square, to WSC, on WSC's visit to Colonel John Brabazon, 4th Hussars, at Aldershot, and his work at Sandhurst, telling him "not to trouble any more about the watch", [which WSC had damaged] as the rough work of Sandhurst was not suitable for a watch made by Dent. Also advising him not to "attend to moneylenders," put their letters into the waste paper basket".

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.

Contains accounts and maps of the First Duke of Marlborough's campaigns and general notes on eighteenth and nineteenth century history.