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.

Letter from WSC (50 Grosvenor Square [London]) to "Mamma" [Lady Randolph Churchill] in which he discusses the wedding of Francis Guest, describes his stay with the [Spender-] Clays, details his plans for his visit to Switzerland with "Jack" [John S Churchill] and expresses his pleasure at the news that "Papa" [Lord Randolph Churchill] is better.

Letter from WSC (Hotel du Bar, Grindelwald [Switzerland]) to "Mamma" [Lady Randolph Churchill] describing his impressions of the scenery, reporting that he and "Jack" [John S Churchill] are being economical and that the rules for the Sandhurst entrance examination have been changed. He asks her to write and tell him how "Papa" [Lord Randolph Churchill] is and says that he is looking forward to her return.

Letter from WSC (50 Grosvenor Square [London]) to "Mamma" [Lady Randolph Churchill] in which he describes his financial situation as "most unsatisfactory" and says that he has been forced to pawn several items; thanks her for sending him photographs of her and "Papa" [Lord Randolph Churchill] in which she says she looks beautiful and describes his plans for Christmas.

Letter from WSC (50 Grosvenor Square [London]) to "Mamma" [Lady Randolph Churchill] in which he says that [Elizabeth] Everest has broken her arm; that he is getting on well with "Grandmamma" [Frances, Duchess of Marlborough], although he is depressed at having to go into the infantry; that he has seen [Adela] Hacket often. He reports that "Jack" [John S Churchill] is keen on photography and that he is looking forward to receiving news of her and "Papa" [Lord Randolph Churchill].

Letter from WSC (Royal Military College [Sandhurst, Camberley, Surrey] on the notepaper of 50 Grosvenor Square) to "Mamma" [Lady Randolph Churchill] in which he expresses his concern about a report on the health of his father [Lord Randolph Churchill], asks her to write to him "unreservedly" on the subject, and says that he worries about the effect of anxiety and travelling on her.

Letter from WSC ([Royal Military College, Sandhurst, Camberley, Surrey] on the notepaper of 50 Grosvenor Square) to [Lord Randolph Churchill] in which he discusses his hopes for his results from Sandhurst and for his father's health and worries which he hopes will be "lulled by the land of the lotus" (quoting one of his father's speeches).

Letter from WSC (50 Grosvenor Square [London]) to "Mamma" [Lady Randolph Churchill] expressing shock at a telegram from Madras [India] reporting the deterioration of [Lord Randolph Churchill's] health, and his intention to see his father with "Jack" [John S Churchill]. He bids her to "keep your pluck and strength up" and to write to him.

Letter from WSC (Royal Military College, Sandhurst, Camberley, Surrey]) to [Lord Randolph Churchill] in which he says that he is looking forward to his father's return, describes the honour of competing for the riding prize at Sandhurst in which he was awarded second place, reports that he is working hard for the examinations and hopes that his father will be pleased with him.

Letter from WSC (The Deepdene, Dorking [Surrey]) to "Mummy" [Lady Randolph Churchill] in which he details his and Jack's [John S Churchill] plans, comments on the kindness of Duchess Lily [Lilian, Duchess of Marlborough, later Lady William Beresford], describes shooting and the examinations at Sandhurst and his determination not to go to Germany.

Letter from WSC (Blenheim Palace) to "Mamma" [Lady Randolph Churchill] describing his stay and the kindness of Sunny [Charles, 9th Duke of Marlborough] and [Albertha] Lady Blandford and wishing her a happy Christmas.

Letter from WSC (Hindlip Hall, Near Worcester) to "Mamma" [Lady Randolph Churchill] informing her that he has written to Colonel [John] Brabazon about entering a cavalry regiment and outlines his reasons for wishing to enter the cavalry and the 4th Hussars. He also says that he is trying to modify his handwriting for her and asks after [Lord Randolph Churchill's] health.

Letter from WSC (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] describing his arrival and his impressions of the regiment and the "military existence".

Letter from WSC (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] discussing arrangements for paying for his outfit, reporting that his name has appeared in the Gazette, that he finds the riding school "fearfully severe" and is suffering from stiffness.

Letter from WSC (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] in which he says that he is suffering from stiffness and reports that he had been put in charge of 80 or 90 horses.

Letter from WSC (4th Hussars, East Cavalry Barracks, Aldershot [Hampshire]) to "Mummy" [Lady Randolph Churchill] in which he says that he is no longer suffering from stiffness, reports that [Lilian, Duchess of Marlborough, later Lady William Beresford] has given him "carte blanche" to get a charger, that he has seen [Frances, Duchess of Marlborough whom he describes as "not particularly malevolent" and that he has declined an invitation to speak to the electors of Barnesbury.

Letter from WSC (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] in which he describes a horse-riding accident and reports that [John] Milbanke is to join his regiment.

Letter from WSC (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] in which he explains the order he placed for her cigarettes and objects to her opinion of steeplechasing as "idiotic" and "fatal", gives details of his anticipated expenses and says that he is looking forward to seeing her in Paris [France].

Letter from WSC (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] discussing financial affairs and his search for a charger; saying that he had made friends and that Dudley Marjoribanks [later 3rd Lord Tweedmouth] has been sent to Canada because of an "inconvenient desire" for an actress.

Letter from WSC (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] expressing concern at the news of "Grandmamma" [Clara Jerome] and at the sad time experienced by his mother and asking her to write to him with information.

Letter from WSC (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] in which he says that his leg is improving, apologises for not being able to deliver her messages to Sir Henry [Drummond] Wolff or Lord Wolverton, reports that Colonel [John] Brabazon has been ill and asks her to reconsider allowing a horse to run under his name.