Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he says that he had not worked hard due to laziness and consequently had received a bad report. He says that her letter "cut me up very much" and explains that he had replied to a letter from "Papa" [Lord Randolph Churchill] but that it had not been posted by the Page and describes his hopes of passing examinations in Geography, French and English dictation and composition. Envelope present.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mamma" [Lady Randolph Churchill] describing the clothes that he has ordered which are illustrated with drawings and asking her to send him money. He encloses a fabric sample [CHAR 28/18/W41]. Envelope present.

Letter from WSC ([Banstead Manor, Newmarket, Suffolk]) to "Mamma" [Lady Randolph Churchill] informing her of his safe arrival, discussing activities he has planned and commenting that "Jack" [John S Churchill] sends her "14 pints of love and 26 brace of kisses". Envelope sealed with black wax.

Letter from WSC (Banstead Manor, Newmarket [Suffolk]) to "Mamma" [Lady Randolph Churchill] in which he says that he and "Jack" [John S Churchill] are enjoying themselves although he expresses his disappointment at not being allowed to shoot and describes [Lady Sarah Churchill, later Sarah Wilson] as being unpleasant towards him. Envelope present.

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he explains that he has not written previously as he did not know her address; reminds her to bring him and "Jack" [John S Churchill] shooting hats; reports that he has received a Fortnum and Mason hamper which has been sent anonymously and suspects that it may be from Lady [Laura] Wilton and describes his hopes for passing his preliminary examination. Envelope present.

Letter from WSC (Reverend James Welldon's, Harrow School [Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he says that he is not "off reports" and that he hopes that she will visit him on his birthday. Envelope at CHAR 28/18/27.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he describes skating on "Ducker" [the swimming pool at Harrow], reports that he has been congratulated [?on passing the Preliminary examination for the army] and asks her to visit him. 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 ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he expresses relief that "Grandpapa" [John, 7th Duke of Marlborough] has reached Brighton [East Sussex] and asks her to visit him as he has been "disappointed so many times about your coming". 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.

Part of a letter from [WSC] ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] asking her to speak to [James] Welldon about taking him "off reports" as he has received satisfactory reports and explains that he is unhappy, commenting "It's all very well for monitors & cricket captains but it is quite a different thing for fourth form boys".

Letter from WSC ([Versailles, France]) to "Mummy" [Lady Randolph Churchill] describing his journey to France, the soldiers he had seen in Versailles and a visit to the "Bon Marche" in Paris. He says that he would like to visit Baron [Moritz] Hirsch and that he almost wrote a letter which would have been "painful" to her due to his "fatigue, the passage, the strange food, the cold, home sickness..." The letter contains several passages and phrases in French.

Letter from WSC ([Versailles, France]) to "Mummy" [Lady Randolph Churchill] thanking her for her telegram, describing riding with [Bernard Minssen] and [Minssen's] mother's approval of his progress in French. The letter contains several passages and phrases in French.

Letter from WSC ([Versailles, France]) to "Papa" [Lord Randolph Churchill] expressing relief at the news that his father has returned safely, describing meetings with Baron [Moritz] Hirsch and [Marquis de] Breteuil and asking him to allow him an extra week's holiday so that he can see "Jack" [John S Churchill].

Letter from WSC ([Brighton, East Sussex]) to "Mamma" [Lady Randolph Churchill] describing his stay with Aunt Lily [Lilian, Duchess of Marlborough, later Lady William Beresford] during which he has met [Arthur] Balfour and Sir George Wombwell. Signed typescript.

Letter from WSC (50 Grosvenor Square [London]) to "Mamma" [Lady Randolph Churchill] informing her that "Missy" [a pet] has recovered and that Captain [Walter] James [tutor at the crammer school to which WSC was sent] has predicted that he will pass [the Sandhurst entrance examination].

Letter from WSC (Grand Hotel, Splendide, Lugano [Switzerland]) to "Mamma" [Lady Randolph Churchill] describing Lugano and saying that he thinks that he is making progress with his French.

Letter from WSC (Continental Hotel, Milan [Italy]) to "Papa" [Lord Randolph Churchill] replying to his letter [see CHAR 1/2/66-68]. WSC says that he will try and alter his father's poor opinion of him through his work and conduct at Sandhurst and describes Milan.

Letter from WSC (Hotel Continental, Milan [Italy]) to "Mama" [Lady Randolph Churchill] in which he expresses his disappointment at [Lord Randolph Churchill's] displeasure with him over his results in the [entrance] examination [for Sandhurst] after his hard work. He discusses his marks in individual subjects and says that he has a chance to alter his father's opinion of him.

Letter from WSC (Hotel Couronne & Poste [?Brigue, Switzerland]) to "Mamma" [Lady Randolph Churchill] in which he says that he is looking forward to going to Sandhurst and that his French is impressive, objects to her comment that he has written "a scrap" [short letter] to "Grandmamma" [Frances, Duchess of Marlborough], expresses his determination to work hard at Sandhurst and asks her to suggest to [Lord Randolph Churchill] that he should be given an allowance.

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 (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] describing the funeral of [Elizabeth] Everest and his sadness at her death. He says that he is looking forward to the time that he has a home, reports that he is "getting on extraordinarily well" and comments on the stigma attached to those who are forced to leave a regiment through unpopularity.

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 [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 "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.