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, 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 "Mummy" [Lady Randolph Churchill] informing her that his toothache has gone, asking after "poor Grandmamma Duchess" [Frances, Duchess of Marlborough] and requesting that she should send him money for subscriptions Annotated "Hurrah for Nunthorpe" [a racehorse which had won the Great Jubilee Stakes at Kempton Park races].

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mummy"[Lady Randolph Churchill] in which he informs her that his [toothache] has got better, asks about the health of various animals and says that [Elizabeth] Everest has sent him a hamper.

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he says that he feels weak and ill and asks her to allow "Woomany" [Elizabeth Everest] to visit him.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] thanking her for allowing "Woom" [Elizabeth Everest] visit him and saying that the doctor has advised him that he should rest and that he would like to come home.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mama" [Lady Randolph Churchill] in which he informs her that he has secured his remove, comments that he has become economical and asks her to sign an enclosure to confirm that he has had measles. Envelope present.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] informing her that he is "all right" although is suffering from a cough. Envelope present.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mummy" [Lady Randolph Churchill] asking about the health of "Grandpapa" [John, 7th Duke of Marlborough] and requesting that [Elizabeth] Everest should make him an appointment with [Sir William] MacCormac as his leg is painful. Envelope present.

Letter from Lord Randolph Churchill (Barton Lodge, Steeple-Aston, Oxfordshire) to [Lady Randolph Churchill] including: the trial for a case of attempted murder at Woodstock [Oxfordshire]; his intention to return to Ireland for Christmas; and his concern over WSC's health.

Letter from Lord Randolph Churchill (Blenheim Palace) to [Lady Randolph Churchill] thanking her for her letters and remarking on [a letter] from WSC. He also discusses: the future marriage of [Lord] Curzon [later 4th Lord Howe] to "Georgie" [Lady Georgiana Churchill, later Lady Curzon and Lady Howe] which he describes as "brilliant"; his poor health; and his opinion that it would be undesirable for her to have dinner with Mrs Beauclere alone; and arrangements for moving into a house.

Letter from WSC to "Mamma" [Lady Randolph Churchill] in which he says that he has nearly recovered from a cough and that he has had dinner with Lady Alfred Churchill.

Letter from WSC ([29 & 30 Brunswick Road, Hove, East Sussex]) to "Oom" [Elizabeth Everest] in which he describes his recent illness, asks her to come and visit him with "Jack" [John S Churchill] and says that he is going to give "Mama" [Lady Randolph Churchill] a "lecture" for not writing to him.

Letter from WSC (29 [& 30] Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] informing her of the date of the school play, asking whether it is "heaven upon earth" without him and of the date that Dr Rouse [Robson Roose] is going to take him to see Dr Woaks [Woakes] and saying that he wants to write to [Lord Randolph Churchill] in India.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] in which he discusses the advice of Dr [Robson] Roose and asks for a riding suit.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] informing her that he has received "the long promised hamper" and has visited the dentist.

Letter from WSC (Tuckers Hotel, Cromer [Norfolk]) to "Mamma" [Lady Randolph Churchill] in which he says that he is unable to walk, swim or paddle because of "Irrispelas" in his legs and that he has to drive himself around in a donkey carriage.

Letter from WSC (Chesterfield Lodge, Cromer [Norfolk]) to "Mama" [Lady Randolph Churchill] in which he says that he is not enjoying himself as his governess is "very unkind and strict and stiff", that he is looking forward to seeing her and that his "temper is not of the most amiable" due to a bilious attack.

Letter from WSC ([29 & 30 Brunswick Road, Hove, East Sussex]) to "Om" [Elizabeth Everest] in which he says that he is feeling weak and "as if I could cry at every thing".

Letter from WSC (29 & 30 Brunswick [Road] Brighton [Hove, East Sussex]) to "Mama" [Lady Randolph Churchill] in which he says that he is "blessed with that inestimable treasure i.e. 'Good Health'" and that he hopes to improve at his studies and at cricket.

Letter from "Winny" [WSC] (29 & 30 Brunswick Road Brighton [Hove, East Sussex]) to "Mama" [Lady Randolph Churchill] in which he says that he has been suffering from a bad cough and expresses concern about [Elizabeth] Everest and "Jack" [John S Churchill].

Letter from [Lady Randolph Churchill](Blenheim Palace) to [Lord Randolph Churchill] in which she discusses the sale of a house in Charles Street; reports that "Mama" [Clara Jerome] is to remain in Paris [France] with Clara [Jerome, later Clara Frewen]; discusses plans to travel to Paris with him;and discusses the health of the baby [WSC].

Letter from [Lady Randolph Churchill](2 Connaught Place [London]) to [Lord Randolph Churchill] discussing the possibility that she may meet him in Monte Carlo [Monaco]; expressing concern about the expense; saying that she will be glad to see him; the opinion of Dr Laking about her recovery [from typhoid]; the possibility that Mrs [Lily] Langtry may divorce; and a pantomime which WSC and "Jack" [John S Churchill] visited during which a poodle was introduced as "Lord Randolph Churchill".