Part of a letter from WSC ([Harrow School, Middlesex]) to [Lady Randolph Churchill] asking her to come and speak to [James] Welldon and "stick up for" him.

Letter from WSC ([Harrow School, Middlesex] on the notepaper of Lexden House, Colchester) to "Mummy" [Lady Randolph Churchill] asking her to come and visit him.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he says that he is getting on well and will sit his preliminary examination for Sandhurst in June, and asks to be allowed to do additional drawing classes and to continue fencing.

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 ([Harrow School, Middlesex]) to "Papa" [Lord Randolph Churchill] in which he informs him that he has been congratulated about the "flukey filly" [the Abbesse, one of Lord Randolph Churchill's racehorses]; says that he would like to enter the army through the militia as he does not enjoy being in the army class at Harrow and reports comments he has heard about his father's parliamentary bill [concerning licensing regulations].

Letter from WSC ([Harrow School, Middlesex]) to "Papa" [Lord Randolph Churchill] in which he informs him that he is not able to sit his preliminary examination this term and that he has been celebrating the success of the Abbesse [one of Lord Randolph's racehorses].

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.