Letter from Lord Randolph Churchill (29 St James' Place [London]) to [Lady Randolph Churchill] including: the annoyance of [Frances, Duchess of Marlborough] at [Lady Randolph] attending a ball; his approval of [his new footman] Frederick; a fight between [20th Lord] Shrewsbury [and Talbot] and [Alfred] Mundy; a planned visit to the zoological [society] by Elizabeth Everest, WSC and [John S Churchill]; and Lord Randolph's opinion that WSC is bored of his holiday.

Letter from John S Churchill (Elstree School, Hertfordshire) to "Mama" [Lady Randolph Churchill] in which he says that "Winny" [WSC] was not allowed to visit him as he had broken a window, reports on his position in his form and says that he is looking forward to returning home for [cricket at] Lords.

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 ([Blenheim Palace]) to "Mamma" [Lady Randolph Churchill] in which he says that he is well and making progress with his lessons and that "Baby" [John S Churchill] is well.

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he says that he was surprised that she visited him in such bad weather and suggests that she might like to come to see the assault at arms or the grand concert. Envelope present.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he expresses approval for a play at the Adelphi theatre [London] called "An English Rose" [by George Sims and Robert Buchanan]. Illustrated with a drawing of a Harrow schoolboy surrounded by luggage.

Letter from "Winny" [WSC] (The Head Master's, Harrow School [Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he asks her to write to him concerning patterns and to send him some "oof" [money].

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he reproaches her for not replying to his last three letters, asks her to make a surgeon's appointment for him, and discusses his intention to sell his bicycle to buy "Dodo", a bull dog.

Letter from Lord Randolph Churchill to [Lady Randolph Churchill] including his lack of success at fishing and a request that she give orders for WSC's hair to be cut short.

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 (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] describing the death of [Elizabeth] Everest from peritonitis. He says that he employed a nurse and that he thinks that his visit "made her die happy" and that he visited "Jack" [John S Churchill] and discusses [Elizabeth Everest's] importance to him and Jack.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] in which he gives the dates of the Easter holidays, describes the weather and a dog given to Miss Thomson and says that he is looking forward to going to Birmingham.

Letter from WSC ([Harrow School, Middlesex]) to Leonie [Leslie, formerly Leonie Jerome] in which he says that he has arrived safely, asks her whether she liked Drury Lane and says that "Jack" [John S Churchill] is well.

Letter from WSC ([2 Connaught Place, London]) to [Lady Randolph Churchill] in which he reports that he has received school prizes for English and Scripture, describes Christmas day and an unwelcome invitation to Blenheim Palace from [Frances, Duchess of Marlborough] and says that "it is very dull without you".

Letter from WSC (45 Hill Street, Berkeley Square [London]) to [Lady Randolph Churchill] informing her that [Elizabeth] Everest is ill and that he and "Jack" [John S Churchill] are staying with Dr [Robson] Roose and feel "destitute".

Letter from WSC (46 Grosvenor Square [London]) to [Lady Randolph Churchill] in which he reports that he has been staying with [Frances, Duchess of Marlborough], that [Elizabeth] Everest has recovered and that he has been given a toy theatre. He discusses plans to see her during term time and a visit to the theatre to see "[HMS] Pinafore" The letter is dated to 1887, but internal evidence suggests that it dates to 1888.

Letter from WSC ([Versailles, France]) to "Mamma" [Lady Randolph Churchill] reproaching her for not writing to him and for forgetting him. Includes a card wishing her a happy new year illustrated with an ink drawing of a woman holding a menu.

Letter from WSC ([Versailles, France]) to "Mummy" [Lady Randolph Churchill] thanking her for her telegram, asking about arrangements for his return home and requesting that she should send his love to "Papa" [Lord Randolph Churchill].

Letter from WSC ([Versailles, France]) to "Mummy" [Lady Randolph Churchill] describing a visit to a morgue with Baron [Moritz] Hirsch and reminding her of her promise [to allow him an extra week's holiday].

Letter from "Winny" [WSC] (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] discussing a cricket match between Gloucestershire and Sussex at which W G Grace is playing.

Letter from "Winny" [WSC] (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] in which he says that he has visited the swimming baths and asks her to send him autographs.

Letter from [Frances, Duchess of] Marlborough (Blenheim Palace, Woodstock) to Mrs [Clara] Jerome reporting on the good progress made by Jennie [Lady Randolph Churchill] and [WSC] who is described as "a very healthy pretty little Child". Envelope present.

Letter from [Frances, Duchess of] Marlborough (Blenheim Palace, Woodstock) to Mrs [Clara] Jerome informing her of the birth of WSC and the safe confinement of Jennie [Lady Randolph Churchill]. She describes WSC's birth and says that Jennie was attended by the Woodstock doctor, that they did not have any baby linen ready and that she will make sure that Mrs Jerome receives a daily bulletin. Envelope present.

Letter from [Lord] Randolph [Churchill] (Blenheim Palace, Woodstock]) to [Clara] Jerome in which he reports on the health of Jennie [Lady Randolph Churchill] and WSC and comments that [Leonard] Jerome has not answered his telegram. Envelope present.