Letter from "Winny" [WSC] ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] describing the extent of an outbreak of measles at school and asking her to allow him to return home, commenting "I should have imagined that as 300 mamas & 300 papas like to have their 'offsprings' home you would like to have me".

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 ([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 ([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 ([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 "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 ([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 (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 (50 Grosvenor Square [London]) to "Mamma" [Lady Randolph Churchill] asking her to persuade "Papa" [Lord Randolph Churchill] to give him an allowance and saying that he has been waiting for a letter from his father, who he hopes will be pleased that he [WSC] has got into the infantry at Sandhurst.

Letter from WSC ([Royal Military College, Sandhurst, Camberley, Surrey]) to "Mamma" [Lady Randolph Churchill] in which he explains that "Grandmamma" [Frances, Duchess of Marlborough] had not given him any money and that he had been forced to borrow some. He expresses his relief that "Papa" [Lord Randolph Churchill] is pleased that he [WSC] has got into the infantry.

Letter from WSC ([Royal Military College, Sandhurst, Camberley, Surrey] on the notepaper of 15 Grosvenor Square) to "Mamma" [Lady Randolph Churchill] in which he says that her letter had made him unhappy and explains that he makes a considerable effort over his letters to "Papa" [Lord Randolph Churchill]. He also discusses his father's refusal to grant him permission to play polo, describes an accident suffered by his riding companion and comments on his own physical feebleness.

Letter from WSC (Blenheim Palace) to "Mamma" [Lady Randolph Churchill] in which he discusses arrangements to come to Hindlip [Worcestershire], describes hunting and shooting and his high opinion of "Sunny" [Charles, 9th Duke of Marlborough] and says that he is looking forward to seeing "Polly" [Adela] Hacket.

Letter from WSC (50 Grosvenor Square [London]) to "Mamma" [Lady Randolph Churchill] in which he says that he does "the model 'son' very well", reports that he will probably accept an invitation from [Samuel, 2nd] Lord Hindlip, and that he and "Jack" [John S Churchill] miss her very much and discusses financial arrangements.

Letter from WSC (Hotel Brittanique, Bruxelles [Brussels, Belgium] on the notepaper of 50 Grosvenor Square) to "Mamma" [Lady Randolph Churchill] describing his journey, Count [Charles] Kinsky's kindness to "Jack" [John S Churchill] and himself and his impressions of Brussels. He expresses relief at the news that [Lord Randolph Churchill] is better but concern that she is unhappy and says that he has got a photograph of her wearing a star in her hair.

Letter from WSC (Royal Military College, Sandhurst, [Camberley, Surrey]) to "Mamma" [Lady Randolph Churchill] in which he reports that he is doing well and that he hopes that his examination results will please "Papa" [Lord Randolph Churchill], asks her to send him money and wishes her success with her concert.

Letter from WSC (Royal Military College, Sandhurst [Camberley, Surrey]) to "Mamma" [Lady Randolph Churchill] in which he reports that he has received a letter from "Papa" [Lord Randolph Churchill] about his [gold] watch and that his father seems "very cross". He also thanks her for her letter saying "You are the best and sweetest mummy in all the world".

Letter from WSC (Royal Military College, Sandhurst [Camberley, Surrey]) to "Mamma" [Lady Randolph Churchill] in which he discusses his plans to visit [London] at the weekend and asks her to write to inform him whether "Papa" [Lord Randolph Churchill] is still angry with him.

Letter from WSC (Royal Military College, Sandhurst [Camberley, Surrey]) to "Mamma" [Lady Randolph Churchill] in which he says that he was "very low" at her departure, that he hopes that she is cheerful and that "Papa" [Lord Randolph Churchill] is better. He informs her that he has been working for his examinations and that he hopes to persuade [Lord Randolph] to allow him to enter the cavalry and says that he would like a letter from her.