Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he says that he is sorry that she could not visit him, asks her to allow [Elizabeth] Everest to bring him ornaments, details the "'oof'" [money] he has spent on furnishing his room and money which he owes, and asks her to send him a P[ost] O[ffice] O[rder] and to ask [James] Welldon to allow him to visit [John, 7th Duke of Marlborough].

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he expresses relief about the health of [John, 7th Duke of Marlborough], says that he is looking forward to seeing [Lord Randolph Churchill] and advises her not to make herself ill with worry.

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] complaining of toothache and informing her that he has secured his remove and become "Head of the Fags".

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mummy" [Lady Randolph Churchill] complaining of toothache and requesting that she should send him money to travel to an appointment with the dentist as he has paid his debts and given up betting.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] informing her that his toothache has gone, asking after "poor Grandmamma Duchess" [Frances, Duchess of Marlborough] and requesting that she should send him money for subscriptions Annotated "Hurrah for Nunthorpe" [a racehorse which had won the Great Jubilee Stakes at Kempton Park races].

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] informing her that he has been in the "deuce of a row" for breaking factory windows and asking her to send him money as he is "absolutely 'oofless'".

Letter from WSC (Inayat Kila [West Pakistan, now Pakistan]) to "Mamma" [Lady Randolph Churchill] in which he describes the fighting at Agrah during which 60 were killed or wounded, informs her that he has been ill and that he has been attached to the 31st Punjab Infantry to command 100 men and hopes that his actions may be noticed. He also comments on the cruelty which he has witnessed about which he comments "I have not soiled my hands with any dirty work". Envelope present.

Letter from WSC (31st Punjab Infantry, Afghanistan) to "Jacko" [John S Churchill] in which he says that he has been busy writing for the Pioneer and the D[aily] T[elegraph], explains that he has been attached to the regiment to replace some of the officers killed, and says that he would like his brother's opinion of his speech.

Letter from WSC (Blenheim Palace) to "Mamma" [Lady Randolph Churchill] marked "secret" informing her that "Sunny" [Charles, 9th Duke of Marlborough] has separated from Consuelo [Duchess of Marlborough, later Consuelo Balsan] and that he has suggested that [Lady Randolph] should stay with her.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he entreats her to allow him to go to Lords cricket ground.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] concerning [James] Welldon's proposal that WSC should spend part of his holidays in France. WSC says that [Lord Randolph Churchill] considers the plan "utter nonsense" and argues that he should not be made to go to "a filthy den". In a postscript he comments "I feel less keen about the army every day. I think the church would suit me much better" and bids her to ask Count Kinsky about fireworks.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he asks her to write [concerning James Welldon's proposal that WSC should spend part of his holidays in France] and to send him some money, and reports that he has been made a Lance Corporal.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he says that he is looking forward to returning home and asks her to make arrangements for shooting at Banstead [Manor, Newmarket, Suffolk].

Letter from WSC ([Blenheim Palace]) to "Papa" [Lord Randolph Churchill] in which he says that he has been to the Lince with "Baby" [John S Churchill] where he picked hyacinths, and that he has seen a snake which [Elizabeth] Everest would not let him kill.

Letter from Blanche [Lady] Airlie (Airlie Castle, Clythe [Scotland]) to Mrs West [Lady Randolph Churchill] congratulating her on WSC's engagement to Clementine [Hozier, later CSC] and commenting on her fondness for Clementine.

Draft letter from Jennie Cornwallis West [Lady Randolph Churchill](2 Norfolk Street, Park Lane [London]) to Lord Furness in which she says that she would be grateful of his assistance in organising the insurance for her scheme ["Shakespeare's England"], explains that her proposals are almost ready and says that [WSC] is going to make a "strong speech" at the Guildhall [London].

Statement of the accounts of the executors of the will of Lord Randolph Churchill namely Jennie Cornwallis West [Lady Randolph Churchill], WSC and John S Churchill which includes the following information: details of purchases, transfer and sale of stock, receipts and payments. Manuscript.

Transcript of the judgement reached in the High Court of Justice Chancery Division before Mr Justice Sargant between Lady Randolph Churchill, WSC and John S Churchill concerning the position of Lady Randolph Churchill under the terms of the will of Lord Randolph Churchill in the event of her remarrying. Typescript.

Notice addressed to Lady Randolph Churchill, WSC and John S Churchill (as executors of the will of Lord Randolph Churchill) informing them that WSC has arranged a mortgage of interest under the will of Lord Randolph. Typescript.

Letter from "Clemmie" [CSC](Admiralty, Whitehall) to "B M" [Lady Randolph Churchill] in which she says that the children have bronchitis, expresses sympathy that she has influenza, comments "as for poor Winston [WSC] his sorrows & anxieties are known to you by the halfpenny Press" and says hat she hopes that she is enjoying her stay with Madame van Andre.