Letter from WSC (35A Great Cumberland Place [London]) to "Mamma" [Lady Randolph Churchill] in which he asks her to keep his secrets and those of others, not to bet or play cards as it will bring "the most terrible misery" and to organise a political dinner for him.

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 ([Blenheim Palace] on the notepaper of 35A Great Cumberland Place) to "Mamma" [Lady Randolph Churchill] in which he says that he has received a telegram from [Sir Alfred] Harmsworth [later Lord Northcliffe] asking whether he would go as correspondent to South Africa and that Oliver [Borthwick] has accepted WSC's terms to be correspondent to the Morning Post.

Letter from WSC (35A Great Cumberland Place [London]) to "Mamma" [Lady Randolph Churchill] informing her of the date on which he leaves for [South Africa] and that he has almost finished ["The River War"] and speculating on the news that [James] Babington has been appointed over [John] Brabazon. Envelope present.

Letter from WSC (35A Great Cumberland Place [London]) to [3rd] Lord Chesham asking him to forward his application for a commission in the Royal Buckinghamshire H[ussa]rs, enclosing certificates [not present] and requesting that War Office reports about him should be considered in the absence of a certificate of moral character.

Letter from WSC (35A Great Cumberland Place [London]) to [3rd] Lord Chesham asking him to sanction his application [see CHAR 28/26/37] to join [the Royal Buckinghamshire Hussars] and to hasten his appointment if possible.

Letter from WSC (RMS Dunotta Castle "en route") to "Mamma" [Lady Randolph Churchill] speculating on the progress of the [Boer War] and on the publication of ["The River War"] and asking her to send copies to Pamela [Plowden, later Lady Lytton] and to [Charles, 9th Duke of] Marlborough. Manuscript in the hand of WSC.

Telegram from WSC (Cape Town [South Africa]) to [Lady Randolph Churchill] requesting that his application to be a Yeomanry Officer should be forwarded to Captain Kikpatrick.

Letter from WSC ("In the train near East London", South Africa]) to "Mamma" [Lady Randolph Churchill] informing her that he is travelling to Natal with Captain [Alexander] Campbell and [John] Atkins from the Manchester Guardian. He observes that the Boer forces have been underestimated and that there will be "a fierce and bloody struggle" and expresses his hope that he is ahead of other newspaper correspondents.

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, Yorktown, [Sandhurst] Camberley, Surrey) to "Mamma" [Lady Randolph Churchill] in which he thanks her for giving him o2, reports that he has seen [Leonie Leslie, formerly Leonie Jerome], Count [Charles] Kinsky, "Grandmamma" [Frances, Duchess of Marlborough], [Lilian, Duchess of Marlborough, later Lady William Beresford] and John Brabazon and that he is suffering from boils.

Letter from "Jack" [John] S Churchill (Elstree School [Hertfordshire]) to "Mama" [Lady Randolph Churchill] in which he thanks her for allowing "Woom" [Elizabeth Everest] to visit him, reports that he has been placed top of his form and says that he is sorry to hear that "Winney" [WSC] has a toothache.

Letter from WSC (Royal Military College, Sandhurst [Camberley, Surrey]) to "Mamma" [Lady Randolph Churchill] thanking her for writing to him. He describes a visit to see the Queen's Birthday Review at Aldershot [Hampshire], the drowning of a cadet and his fall into the lake.

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 ([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.