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 says that "Clemmie" [Clementine Hozier, later CSC] is "vy happy and beautiful", thanks her for her support "at a critical period in my emotional development"; expresses relief that the [wedding] ceremony is over and that George [Cornwallis-West] had said that "he could wish me no better wife or happier days than he had found in you".

Letter from WSC ([Italy] on the notepaper of the Board of Trade) to "Mamma" [Lady Randolph Churchill] discussing the sale of the house at Bolton Street and saying that he and CSC are happy [on their honeymoon] and have "loitered and loved - a good & serious occupation for which the histories furnish respectable precedents".

Telegram from WSC (Woodstock [Oxfordshire]) to Mrs [Cornwallis-]West [Lady Randolph Churchill] expressing concern for her health and reporting that "Sunny" [Charles, 9th Duke of Marlborough] would like her to visit [Blenheim Palace] for New Year. Envelope present.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] asking her to reimburse him for money spent on a visit to the doctor's and detailing what he has spent.

Letter from Lord Randolph Churchill (Tarbes [France]) to [Lady Randolph Churchill] including: his impressions of Tarbes, [the Marquis de] Breteuil's unease at the possible effect of the arrival of Jeanne Granier, a French actress, on the local electorate; his desire that WSC should read during his school holidays and his outrage at the marriage of the Duke of Montrose.

Letter from WSC (29 & 30 Brunswick [Road] Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] asking about her sea crossing and saying that he is looking forward to the holidays.

Letter from "Winny" [WSC] (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] discussing the popularity of the Primrose League at school and asking whether he might join the London branch.

Letter from "Winny" [WSC] (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] begging her to write to Miss Thomson to persuade her to allow him to attend the Jubilee and including his suggestions for the content of her letter Illustrated with drawings of soldiers and a face. Envelope present.

Essay by WSC on the physical geography and history of Palestine [Israel] and its people in the time of John the Baptist (25 BC to AD 1).

Letter from Lord Randolph Churchill (Makerstoun House, Kelso [Roxburghshire]) to Jennie [Lady Randolph Churchill] including: the success of a racehorse called Renard; the people he has met; comments on the British government's policy on Uganda and a visit to Harrow to see WSC and John S Churchill at which [James] Welldon had discussed the likelihood that WSC would pass his next examination.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lord Randolph Churchill] in which he expresses his pleasure that he is going to Harrow [School] rather than Winchester [School]; discusses his progress with Euclid, arithmetic and Greek; reports that he is to play roles in plays by Moliere and Aristophanes and says that he wished that his father could attend the distribution of prizes.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mama" [Lady Randolph Churchill] in which he reports on his progress with Greek, Euclid and Latin.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] in which he says that he would like her and [Lord Randolph Churchill] to attend the distribution of prizes, discusses his birthday party and the future examinations, and asks for more of her autographs as "there is rather a demand for them here".

Letter from "Winny" [WSC] ([29 & 30 Brunswick Road, Hove, East Sussex]) to "Mama" [Lady Randolph Churchill] thanking her for a P[ostal] O[rder] and detailing his examination marks and positions. Envelope present.

Part of a letter from [WSC] (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] in which he reports that he has begun to learn Greek verbs ending in "mi", describes a visit to the theatre with [Lady Wimborne, earlier Cornelia, Lady Guest and Lady Cornelia Churchill] and hints that he would like to be given an illustrated history of the American [civil] war as a birthday present.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] in which he says that he intends to write to [Lord Randolph Churchill] and that he is rehearsing "the Greek play" ["The Knights" by Aristophanes].

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] in which he reports that [Lord Randolph Churchill] has taken him to the Orleans Club.

Letter from WSC (105 Mount Street [London]) to "Mamma" [Lady Randolph Churchill] in which he says that he enjoyed seeing her and that he has received letters from [Joseph] Chamberlain which he is working on [for the biography of Lord Randolph Churchill].

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.