Letter from "Jack" [John S Churchill] (Harrow School) to WSC, on WSC's failure in the Sandhurst entrance examination.

Letter from "Jack" [John S Churchill] (Harrow School) to WSC, school news, particularly outbreak of scarlet fever.

Letter from "Jack" [John S Churchill] to WSC, on publication of letter from WSC in "The Harrovian".

Letter from "Jack" [John S Churchill] to Lady Randolph Churchill, on outbreak of scarlet fever at Harrow, Jack's birthday, and WSC's visit to Harrow.

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 [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 James Welldon ([Harrow School, Middlesex]) to Lady Randolph [Churchill] in which he discusses arrangements concerning WSC and an appointment with [Bernard] Minssen. He observes that WSC must work while he is staying with [Bernard] Minssen to improve his French, and urges that he should only be allowed to see limited numbers of English-speaking people and says that he is determined that WSC should be accepted by Sandhurst.

Letter from James Welldon (Harrow School [Middlesex]) to Lady Randolph [Churchill] in which he suggests that WSC should spend part of his holiday in France.

Letter from James Welldon (Harrow School [Middlesex]) to Lady Randolph [Churchill] suggesting that WSC should be sent to spend part of his holiday with Madame Elmering in Rouen, France and recommending that he should be urged to work hard to increase his chances of being accepted into Sandhurst.

Postcard from "Jack" [John S Churchill] to Lady Randolph Churchill asking her to visit him and reporting that "Winey" [WSC] has written to tell him that he is going to take Sandhurst "by storm".