Letter from WSC ([Versailles, France]) to "Mamma" [Lady Randolph Churchill] in which he promises to send her a copy of the Harrovian which includes a "very feeble" reply to his letter and thanks her (in French) for sending him 50 francs and comments that her letter was "foudrayante et inouie [devastating and unexpected]".

Letter from WSC ([Harrow School, Middlesex]) to [Lady Randolph Churchill] expressing his pleasure that she is coming to visit him and promising her that he will be "specially got up for the occasion".

Letter from "Jack" [John S Churchill] ([Brighton, East Sussex]) to "Papa" [Lord Randolph Churchill] asking him to send him autographs and photographs and reports that Miss Thomson considers that "Winny" [WSC] is "a very good boy" and that WSC is going to write a Greek play for Christmas.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] describing his journey and discussing arrangements to have his toy theatre sent to him.

Letter from "Jack" [John S Churchill] ([Harrow School, Middlesex]) to "Mama" [Lady Randolph Churchill] in which he says that "Winney" [WSC] is taking "all kinds of medicines" and sends his love.

Letter from [John S Churchill] ([Harrow School, Middlesex]) to "Mama" [Lady Randolph Churchill] in which he discusses arrangements to return home and says that "Winney" [WSC] is unwell.

Letter from Lord Randolph Churchill ([Rutland Cottage] Newmarket [Suffolk]) to [Lady Randolph Churchill] thanking her for her letters, describing the races at Newmarket, discussing the sale of a house and instructing her to take care of the baby [WSC].

Letter from Lord Randolph Churchill ([Rutland Cottage] Newmarket [Suffolk]) to [Lady Randolph Churchill] describing his success at the races and expressing his pleasure that the baby [WSC] is better.

Letter from Lord Randolph Churchill to [Lady Randolph Churchill] including: advice about whether she should go to Sandown [Isle of Wight]; the eagerness of [John, 7th Duke of Marlborough] that the quarrel between Lord Randolph and Cornelia [Lady Guest, later Lady Wimborne, earlier Lady Cornelia Churchill] should be resolved; the time of his arrival in London and his pleasure at receiving "such flourishing accounts" of WSC.

Letter from Lord Randolph Churchill to [Lady Randolph Churchill] thanking her for her letter and describing the "Ruin" as "out of order". He expresses the hope that [Elizabeth] Everest's friends are "respectable" and asks [Lady Randolph] to instruct [Elizabeth Everest] not to allow WSC to play with other children, and says that he is feeling better.

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 "Winny" [WSC] ([29 & 30 Brunswick Road, Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] in which he says that Miss Thomson thinks that he should not return home to attend the Jubilee and asks her to write to persuade her to the contrary, commenting "I am in a ferment about coming home".

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] informing her of his progress in the rifle drill and asking her to come and visit him. Includes illustration of soldiers and a cannon on the dorse.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] saying that he has written to a boy at Harrow School and obtained information about the school and its entrance examination and describing underwater swimming and a concert at which George Grossmith and Weedon Grossmith performed.

Letter from [John S Churchill] ([Harrow School, Middlesex]) to "Mama" [Lady Randolph Churchill] reporting that "Winney" [WSC] is going to take a medical examination and that he is hoping for a quiet day, commenting "I do not get much peace while he is here".

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he apologises for not writing earlier as he has been busy and has been "on lines" for two half holidays and asks her to visit him. Envelope present.

Letter from Lord Randolph Churchill (50 Grosvenor Square [London]) to [Lady Randolph Churchill] describing his journey and a hunting expedition with the Meath hounds and discussing his bedroom furniture. He adds that he has sent WSC a copy of his Sandhurst examination marks commenting that he should be pleased with his position of eighth despite criticism for impunctuality.

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he says that he is enjoying being in [James] Welldon's house and asks her to send him money and to visit him.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he says that he is well and describes his success at a rifle range.

Letter from WSC ([Harrow School, Middlesex]) to "Mama" [Lady Randolph Churchill] in which he reports that he has fallen on the back of his head and asks her to come and visit him.

Letter from Lord Randolph Churchill (Le Nid [Monte Carlo, Monaco]) to [Lady Randolph Churchill] describing a trip to Nice [France] and the people he has met who include "Ronny" [Ronald] Greville and attempts by the Duchess of Montrose to "take the Nid by storm". He also discusses WSC's riding expenses and asks her to draw WSC's attention to "expressions of authority".

Letter from WSC ([Harrow School, Middlesex]) to "Mama" [Lady Randolph Churchill] in which he says that he has received no information about her or Grandpapa [John, 7th Duke of Marlborough] and asks her to write to him by return of post and send him money.