Letter from WSC (Omdurman [Sudan]) to "Mamma" [Lady Randolph Churchill] discussing his orders to return to Atbara which are a result of his unpopularity with the Sirdar [Sir Herbert Kitchener] and the possibility that the French are in Fashoda.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Papa" [Lord Randolph Churchill] in which he says that he is getting on well and that "Mamma" [Lady Randolph Churchill] sent him some oranges from Monte Carlo [Monaco] and that he has received a letter from "Jack" [John S Churchill] about Elstree [Hertfordshire].

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] informing her that he has secured his remove and has started learning German and commenting on the success of the "Habbesse" [the Abbesse, one of Lord Randolph Churchill's racehorses].

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] discussing arrangements for her to visit him when she returns to England and requesting Latin dictionaries.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] in which he says that he is looking forward to seeing her and [Lord Randolph Churchill], discusses the Harrow School entrance examination and his progress at school and requests dictionaries.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] in which he says that he is looking forward to his toy theatre arriving, requests equipment for it and asks for money.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] discussing his prospects for the Harrow School entrance examination.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lord Randolph Churchill] discussing his prospects for the Harrow School entrance examination, detailing his progress with Virgil's Aeneid, Euclid, mathematics and other subjects and asking his father to visit him.

Letter from Lord Randolph Churchill (Hotel Bristol, Rome [Italy]) to [Lady Randolph Churchill] in which he expresses his admiration for [Charles] Parnell's manifesto and speculates on the future of the Home Rule alliance and the likelihood of a dissolution of parliament. He describes an evening spent with [1st Lord] Dufferin [and Ava] and says that he has received a letter from WSC "giving a glowing account of himself".

Letter from WSC (Bangalore [India]) to "Mamma" [Lady Randolph Churchill] including: the postponement of his leave; his decision to visit Sir Herbert Kitchener in Egypt; a request for letters of introduction; discussion of his reasons for wishing to return to England during his leave; financial affairs; reading and his gratitude at receiving copies of the Annual Register.

Letter from WSC (Bangalore [India]) to "Mamma" [Lady Randolph Churchill] including: his injury while playing polo; a list of the books he has read while in India; his method of constructing "a scaffolding of logical and consistent views" through studying the Annual Register; observations on education; and arrangements for caring for "Firefly" [a horse] which he is sending to England.

Letter from WSC (Harrow on the Hill [Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he details the form positions he expects in his examinations to secure his "Remove" and says that he hopes that [Lord Randolph Churchill] will visit for the "Cock House Match" [a football match]. Envelope present.

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] asking her to send him money for subscriptions as "you promised I should not be different to others" and informing her of his position in class.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he describes his progress at school, (including in mathematics in which he is studying stocks), a "Sale by Auction" and a paper chase and says that he hopes she is enjoying her "spree on the continong [continent]".

Letter from WSC ([Harrow School, Middlesex]) to "Papa" [Lord Randolph Churchill] asking him to write to [James] Welldon concerning his school house and describing a "sham fight" with other schools.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he expresses his disappointment that she did not come to visit him and asks her to visit him on the next day.

Letter from WSC (Reverend [James] Welldon's, Harrow School [Middlesex]) to "Papa" [Lord Randolph Churchill] discussing arrangements for speech day and the areas of the school which he could show his father.

Letter from WSC (Reverend [James] Welldon's, Harrow School [Middlesex]) to "Mamma" [Lady Randolph Churchill] asking her to persuade [Lord Randolph Churchill] to attend speech day and to allow [Elizabeth] Everest to visit him.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] reproaching her for forgetting him, asking her to send him money, to arrange an appointment with the oculist, and to sign a form permitting him to begin fencing.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Papa" [Lord Randolph Churchill] informing his father that he has secured his remove.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mama" [Lady Randolph Churchill] informing her that he has secured his remove and thanking her for sending him oranges.

Letter from "Winny" [WSC] (The Head Master's, Harrow School [Middlesex]) to "Woom" [Elizabeth Everest] informing her of his safe arrival and detailing the clothes he has ordered.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mamma" [Lady Randolph Churchill] promising to give up smoking for six months, reporting that "Jack" [John S Churchill] is "very low" and describing the decoration of his room. Illustrated with drawings of Harrow school boys and uniform.

Letter from "Winny" [WSC] ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he explains that he has been working very hard and details his hopes for success in individual subjects and comments that he is "afraid some enemy hath sown tares in your mind".

Letter from WSC (Inayat Kila [West Pakistan, now Pakistan]) to "Uncle Bill" [Lord William Beresford] in which he describes his luck at being posted to "the hardest fighting that the frontier has seen for many years", gives an account of the fighting in which he has been involved, and says that despite the difficulty of commanding the regiment without speaking Hindustani, he hopes that "the moral effect of my presence will alone inspire confidence".