Letter from Jack Milbanke, Eartham, Chichester, to WSC, on WSC's troubles at Harrow, hunting, and on Milbanke's Commission in the Sussex Militia.

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] to WSC, on publication of letter from WSC in "The Harrovian".

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 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 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 Lady Randolph Churchill, 2 Connaught Place, London, to WSC, congratulations on obtaining Remove [into the First Division of the Fourth Form at Harrow], hoping that he would continue to work. Asking him to write at least twice a week.

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 Lady Randolph Churchill, Banstead, to WSC, apologies for not visiting him at Harrow, and advising him not to sell his bicycle and buy a bulldog puppy "a dog is sometimes a nuisance".

Letter from Lady Randolph Churchill, Iwerne Minster House, Blandford, to WSC, on his school report "You must try & have a better one next term as Papa will be back & will expect glowing accounts of yr work." Also commenting on a day's hunting, and "cutting a lovely somersault" at the 3rd fence.

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".

Letter from Lord Randolph Churchill, 2 Connaught Place, London, to WSC, congratulations on WSC's success in the Harrow School Fencing competition. "I only hope fencing will not too much divert your attention from the Army Class.

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 Maggie Gooderidge, former servant of WSC's family, "better known as Maggie from Blenheim" (Chadderton Street, London W1) to WSC, with sympathy on his road accident in New York [United States] and a reminiscence about his childhood.

Letter from [Lady Randolph Churchill] to [Lord Randolph Churchill] in which she reports that [Frances, Duchess of Marlborough] has read out Lady Londonderry's comments about him, says that she has avoided seeing [the Duke of] Connaught [and Strathearn] and that WSC has been behaving ridiculously by saying to Cottlehurst "Goodbye little chap".

Letter from [Lady Randolph Churchill] (Hotel Meurige, Calais [France]) to [Lord Randolph Churchill] in which she describes her journey with WSC, a night spent in the "worst" hotel in Calais and her fears for their safety.

Letter from [Lady Randolph Churchill] (Blenheim Palace) to [Lord Randolph Churchill] in which she comments on WSC's "naughty" behaviour, recommends that he should return to London and reports that the MP for Manchester, Mr Burley, has died.

Letter from [Lady Randolph Churchill] (2 Connaught Place [London]) to [Lord Randolph Churchill] including: the decision of her mother [Clara Jerome] to leave and request that Clara [Frewen, earlier Clara Jerome] should not be left alone; John Delacour's poor health and financial difficulties; a message from Henry Hoare; and her relief to "get Winston [WSC] off her hands" .