Letter from WSC (Harrow on the Hill [Middlesex]) to "Mamma" [Lady Randolph Churchill] informing her of his safe return, asking her to allow [Elizabeth] Everest and "Jack" [John S Churchill] to visit him, and commenting on his bad luck in being obliged to leave [the wedding of Lady Sarah Churchill, later Sarah Wilson to Gordon Wilson] when he was "making an impression on the pretty Miss Weaslet".

Letter from WSC (Harrow on the Hill [Middlesex]) to "Mamma" [Lady Randolph Churchill] asking her not to send him to Paris [France] before Christmas warning her that if she does "the holidays will be one continual battle".

Letter from WSC (Harrow on the Hill [Middlesex]) to "Mamma" [Lady Randolph Churchill] concerning the possibility that she might send him to Paris [France] before Christmas, asking her to consider his happiness "There are other and higher things in this world than learning, more powerful agents than the Civil Service Commissioners".

Letter from WSC (4th Hussars [Bangalore] India) to "Mamma" [Lady Randolph Churchill] including discussion of financial affairs, their extravagance and lack of money and the possibility of transferring to a regiment which would enable him to pursue a parliamentary career. Envelope present.

Letter from WSC (4th Hussars [Bangalore] India) to "Mamma" [Lady Randolph Churchill] discussing financial affairs, his acceptance of liability for a loan provided the amount is shared with "Jack" [John S Churchill], and her extravagance. Envelope present.

Letter from WSC ([Harrow School, Middlesex] on the notepaper of Banstead Manor, Newmarket) to "Mamma" [Lady Randolph Churchill] in which he apologises that he has not had the time to write as he has been busy with the "assault at arms", informs her that he is depressed that the examinations have finished and encloses an account of his necessary end of term expenses. Envelope present which includes a note "Mind and come on Thursday and slang me and kiss me Mummy".

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] asking her to come and visit him on Thursday and suggesting that they should go to the King's Head for lunch. The letter "M" at the start of the letter is composed of an illustration depicting a boy kicking a football.

Letter from WSC ([29 & 30 Brunswick Road, Hove, East Sussex]) to "Mama" [Lady Randolph Churchill] in which he details the terms under which he would be prepared to have a tutor during the holidays (including "That I don't do a stoke of work").

Letter from WSC ([29 & 30 Brunswick Road, Hove, East Sussex]) to "Mama" [Lady Randolph Churchill] responding to the news that "Mr Pest" [James Best] is to be his tutor during the holidays and promising to behave well provided that he is not made to work.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] in which he asks where [Lord Randolph Churchill] is and describes his financial situation and progress at swimming and with Euclid.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] in which he reminds her to send him a copy of "She" and says that he is contemplating writing a play to be performed at Christmas.

Letter from [John S Churchill] (Elstree School [Hertfordshire]) to "Mama" [Lady Randolph Churchill] describing a visit from "Winney" [WSC] and asking about her plans for the holiday, commenting "Do let me keep with Winney whatever happens".

Letter from Lord Randolph Churchill (2 Connaught Place [London]) to [Lady Randolph Churchill] thanking her for her letter and discussing his future visit to Paris [France] with [Henry] Chaplin and "Tommy" [WH] Trafford. He also reports on WSC's health and enjoyment of a locomotive steam train; a successful speech he has made in Parliament which had pleased the Whigs; and comments about "GOM" [Grand Old Man, William Gladstone] "He is the wickedest old devil any country ever produced".

Letter from WSC (Bangalore, [India]) to "Mamma" [Lady Randolph Churchill] in which he says that he does not intend to be a professional soldier and therefore would like either to enjoy himself or "see active service" and that he would like further details about the possibility of going to Egypt with [Sir Herbert] Kitchener and expresses his gratitude for his mother's actions on his behalf. He discusses the anniversary of the battle in which he participated in Cuba.

Telegram from Caryl [Ramsden] (Wadhamed [Wad Hamid, Sudan]) to [Lady Randolph Churchill] reporting "Winston [WSC] arrived both very fit advance tomorrow".

Letter from WSC (North of Shabluka [Sudan]) to "Mamma" [Lady Randolph Churchill] discussing the imminent battle and [Sir Herbert] Kitchener's disapproval of his actions and enclosing a letter [not present] for the Morning Post.

Letter from WSC ([29 & 30 Brunswick Road, Hove, East Sussex]) to [Lady Randolph Churchill] in which he reports that he has nearly recovered and asks whether he may return to school late in order to see her during his holidays as "a week would make no difference to any one but you & me".

Letter from WSC to "Mamma" [Lady Randolph Churchill] in which he says that "Womany" [Elizabeth Everest] says that he is looking well that he is looking forward to seeing her and describes his symptoms.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] reporting that he has passed the entrance examination for Harrow School and describing the examination and a meeting with [James] Welldon. Envelope present.

Letter from WSC ([29 & 30 Brunswick Road, Hove, East Sussex]) to [Lady Randolph Churchill] in which he says that he has had mumps but hopes that he will be able to return home for easter.

Letter from WSC ([Harrow School, Middlesex]) to "Papa" [Lord Randolph Churchill] thanking him for sending him game, reporting that the army class master thinks that he will pass his examination and that he has been forced to wear a truss and commenting on the Eccles [Lancashire] by election [in which a Conservative lost the seat to a Liberal].

Letter from "Jack" [John] S Churchill (Harrow on the Hill [Middlesex]) to "Mama" [Lady Randolph Churchill] in which he reports that "Winney" [WSC] appears to be enjoying Sandhurst despite a boil on his face and seems to have grown two inches. He also says that a Constitutional Club is to be opened the following week.

Letter from Lord Randolph Churchill (Novar, Evanton, Ross-shire [Ross and Cromarty, Scotland]) to [Lady Randolph Churchill] thanking her for her letters to him and requesting that she should thank WSC for his letter, approving of her decision to send "Jack" [John S Churchill] to Brighton [East Sussex] and predicting that [Sir] Charles Legard's letter [to the newspapers] will not harm him.

Letter from Lord Randolph Churchill (2 Connaught Place [London]) to [Lady Randolph Churchill] including the end of excitement in the French Chamber at the election of the new president; a meeting about the unemployed in [South] Paddington [London] which resulted in the establishment of a relief fund; his intention to see WSC when he visits Brighton [East Sussex] and an outline of his planned itinerary.

Note from WSC (on the notepaper of the 4th Hussars, India) to "Mamma" [Lady Randolph Churchill] listing arguments in favour of him joining the Nile expeditionary force in Egypt and protesting that he would have been recalled from leave if he had committed an offence [by going to Egypt without having his leave approved].