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 ([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 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.

Letter from WSC ([Harrow School, Middlesex]) to "Mama" [Lady Randolph Churchill] in which he says that he is getting on well and asks her to send him money for a visit to see "Jack" [John S Churchill].

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mamma" [Lady Randolph Churchill] asking her to make arrangements for someone to attend speech day.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he expresses pleasure that he is not going abroad for his holidays, describes arrangements for a camp and asks her to give him money and to buy him a pair of butcher boots. He encloses the camp regulations [not present] and suggests that she might approach officers at Aldershot [Hampshire] to introduce themselves to him.

Letter from WSC ([Cliveden, Buckinghamshire]) to "Mummy" [Lady Randolph Churchill] in which he informs her that he is well, describes a punting trip with [Lady Sarah Churchill, later Sarah Wilson] and a visit to Newmarket [Suffolk].

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] reproaching her for not replying to his last three letters, commenting "If [Elizabeth] Everest did not write to me I should hardly imagine that there was such a place as Banstead [Manor, Newmarket, Suffolk], and asking her to contact him about a [surgeon's] appointment.

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 WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] informing her that he has won a cup for fencing, thanking her for oranges and reporting that he has to wear glasses.

Letter from WSC ([Harrow School, Middlesex]) to "Mama" [Lady Randolph Churchill] informing her that he is working hard at his fencing in which he represents the school, asks her to send his love to Lady [Laura] W[ilton] and to send him money to "replenish the exchequer".

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] informing her of his safe arrival and reporting that Mr [H O] Davidson thinks it likely that he will secure his remove. Envelope present.

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] apologising for not writing to her sooner and expressing pleasure at the news that she is returning home. Envelope present.

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he informs her that he has moved into [James] Welldon's house, describes his room and various items he would like "Woom" [Elizabeth Everest] to send to him. Envelope present.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] informing her that he is "happy and quite well" and asking her to allow [Elizabeth] Everest to buy items for his room. Envelope present.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he informs her that he has joined the "Army class" and that he is learning French and geometrical drawing and studying for the Shakespeare prize. Envelope present.

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] asking her to allow [Elizabeth] Everest to send his bicycle for a "grand field day" at Wimbledon [Surrey] and to sign an order [?to permit him to fence]. Envelope present.

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] thanking her for sending him an order [?to permit him to fence] and asking her to visit him on Saturday. In a postscript he informs her that he has won a rifle shooting competition and includes a diagram of the position of his bullets. Includes envelope.

Letter from WSC (Harrow on the Hill [Middlesex]) to "Mama" [Lady Randolph Churchill] asking her to visit him as he would like her to "jaw" [James] Welldon about keeping him "on reports" and discussing arrangements for appointments with the doctor and dentist. In the hand of [James] Milbanke. Envelope present.

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he says that he enjoyed "Papa's" [Lord Randolph Churchill's] visit and that he is looking forward to the holidays. Envelope present.

Letter from WSC (Reverend James Welldon's, Harrow School [Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he says that Welldon is determined that WSC should get his remove and that he hopes that he will be allowed to take a holiday on his birthday. Envelope present.

Letter from WSC ([Harrow]) to "Mama" [Lady Randolph Churchill] describing the contents of an examination he has taken and his hopes that he has passed. He lists the essay questions which were set and comments on his luck that he had revised the map of New Zealand. Envelope present.

Telegram from WSC (Harrow School [Middlesex]) to [Elizabeth] Everest informing her that he is well and that he has secured his remove.

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.