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 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 (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 (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] 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 discusses financial affairs, the payment of his allowance and her irritation with him. He informs her that he is attending the levee of [Albert Edward, Prince of Wales] and describes the celebrations for Queen Victoria's birthday which will be attended by "Molly" [Adela] Hacket and his progress at polo.

Letter from WSC (Blenheim Palace) to "Mamma" [Lady Randolph Churchill] in which he describes the races at Ascot [Berkshire], the attempts of Lady Angela [St Clair-Erskine] to "captivate" "Sunny" [Charles, 9th Duke of Marlborough] and a visit to the grave of "Papa" [Lord Randolph Churchill] at Bladon [Oxfordshire].

Letter from WSC ([Harrow School, Middlesex] on the notepaper of Banstead Manor, Newmarket, Suffolk) to "Mamma" [Lady Randolph Churchill] in which he says that he has arrived safely, that he has written to "Papa" [Lord Randolph Churchill] who he hopes will not continue to be angry and that he hopes that she will feel better soon.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] thanking her for allowing "Woom" [Elizabeth Everest] to visit him although he says that he was disappointed at not seeing her [Lady Randolph] and asks her to visit him.

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.