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 Pamela [Plowden, later Lady Lytton] to Lady Randolph Churchill quoting from an article about WSC, referring to WSC's complaint that she never writes to him and commenting on Lady Randolph's kindness towards them.

Telegram from "Jack" [John S Churchill] (Edgware Road [London]) to Lady Randolph Churchill reporting that Oliver [Borthwick] has telegraphed that WSC has been captured by the Boers. He reassures her that WSC was not wounded but displayed "splendid" bravery.

Letter from [Frances, Duchess of Marlborough] (Branksome Dene, Bournemouth [Hampshire]) to [Lord] Randolph [Churchill] discussing arrangements for his return home and her poor health; asking whether he and Jennie [Lady Randolph Churchill] would like "Lily" [Lilian, Duchess of Marlborough, later Lady William Beresford] to care for [WSC and John S Churchill] and expressing a desire to see him.

Letter from [Frances, Duchess of Marlborough] (Grand Hotel, Scarborough [Yorkshire]) to [Lord] Randolph [Churchill] in which she says that she is unsure where to send letters to him; says that she thinks that "Jack" [John S Churchill] has enjoyed spending time with her; recommends that he should advise WSC about "diligence & hard work...economy & self denial" and expresses anxiety about his health.

Letter from [Frances, Duchess of Marlborough] (50 Grosvenor Square [London]) to [Lord Randolph Churchill] including: her health and plans to take "Jack" [John S Churchill] to the sea; news of WSC and her attempts to discipline him "especially ab[ou]t money"; her anxiety about him and appreciation for his letters; news about Erick Curzon and horse racing.

Letter from [Lady Randolph Churchill] (Iwerne Minster House, Blandford [Dorset]) to "Jack" [John S Churchill] in which she says that she has received a letter from Colonel [John] Brabazon enclosing a letter from Sir Bindon Blood which praised WSC, commenting that "he was doing the work of 2 ordinary subalterns", and said that it was likely that WSC would be awarded the Victoria Cross or the DSO [Companion of the Distinguished Service Order]. See also CHAR 28/111/2-3. Signed manuscript.

Letter from Lord Randolph Churchill (Government House, Bombay [India]) to [Lady Randolph Churchill] including: birthday greetings; comments on the "adventures" had by WSC; arguments between Leonie [Leslie, earlier Leonie Jerome] and the Leslie family; his opinion of Parsee practices; descriptions of his social engagements and those he has met, who included leading native politicians; his itinerary and a request that she should tell "Winnie" [WSC] that he has received his letter.

Letter from Lord Randolph Churchill (Residency Lucknow [India]) to [Lady Randolph Churchill] including: thanks for her letters and a request that she thank "little Winny" [WSC] for his letter which Lord Randolph describes as well written; his annoyance at a letter from [Sir Henry Drummond] Wolff; his poor opinion of the English in Lucknow; and observations on a meeting with the natives of Lucknow.

Letter from Lord Randolph Churchill (Bedford Hotel, Brighton [East Sussex]) to [Lady Randolph Churchill] expressing his distress that WSC's fever has returned, enclosing a telegram [not present] and including directions for [Dr Robson] Roose as to where he is staying.

Letter from CSC to WSC stating that Anita Leslie is Sir Shane Leslie's daughter, that "I believe she has done very good service" in North Africa and Alsace [ France], recommending that WSC asks her to luncheon, and regretting that she will not be there. [Initialled typescript].

Note from Kathleen Hill [Personal Secretary to WSC] to John Colville [Prime Minister's Private Secretary] informing him that Anita Leslie has accepted the invitation to lunch at Chequers [Buckinghamshire] on Friday and asking him to arrange for the car to call for Miss Leslie at 12.20 pm and to combine her with Commander Guest if he accepts. [initialled typescript] With further ms annotations by Kathleen Hill and John Colville regarding arrangements.

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.