Letter from "Winny" [WSC] (The Head Master's, Harrow School [Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he asks her to write to him concerning patterns and to send him some "oof" [money].

Letter from WSC ([Harrow School, Middlesex]) to "Mama" [Lady Randolph Churchill] in which he says that he has received no information about her or Grandpapa [John, 7th Duke of Marlborough] and asks her to write to him by return of post and send him money.

Letter from WSC ([Harrow School, Middlesex]) to "Mama" [Lady Randolph Churchill] in which he says that he is getting on well and asks her to send him money for a visit to see "Jack" [John S Churchill].

Letter from WSC ([Harrow School, Middlesex]) to "Mama" [Lady Randolph Churchill] informing her that he is working hard at his fencing in which he represents the school, asks her to send his love to Lady [Laura] W[ilton] and to send him money to "replenish the exchequer".

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mamma" [Lady Randolph Churchill] describing the clothes that he has ordered which are illustrated with drawings and asking her to send him money. He encloses a fabric sample [CHAR 28/18/W41]. Envelope present.

Letter from WSC (Hotel Couronne & Poste [?Brigue, Switzerland]) to "Mamma" [Lady Randolph Churchill] in which he says that he is looking forward to going to Sandhurst and that his French is impressive, objects to her comment that he has written "a scrap" [short letter] to "Grandmamma" [Frances, Duchess of Marlborough], expresses his determination to work hard at Sandhurst and asks her to suggest to [Lord Randolph Churchill] that he should be given an allowance.

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 (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.

Telegram from Lord Randolph Churchill (Hong Kong) to the London and Westminster Bank informing them that Lady Randolph Churchill would like all Jerome payments transferred to his account.

Letter from Mary [Lady Curzon](Viceroy's Camp [India]) to Jennie [Lady Randolph Churchill] in which she wishes her happiness in her marriage [to George Cornwallis-West] and says that she hopes that her financial affairs have improved through the success of [the Anglo Saxon] Review; Lady Margaret Ewing's lack of money; and the work of George [Lord Curzon, later Lord Curzon of Kedleston as Viceroy of India].

Letter from John Morley (57 Elm Park Gardens, South Kensington [London]) to Lady Randolph Churchill discussing financial affairs.

Letter from Clara Jerome ([Paris, France]) to Lord Randolph Churchill in which she informs him that [Leonard Jerome] has given his consent to him marrying [Jennie Jerome, later Lady Randolph Churchill] but warns him that he is unaware of the objections posed by [John, 7th Duke of Marlborough]. [Mr Jerome] has offered a settlement of 2,000 pounds per year.

Cheques returned to Lord Randolph Churchill giving details of the amount, the recipient and the date. Cheques to individuals are signed on the dorse by the recipient and include: Thomas Cook, George Wombwell and Henry Chaplin.

Christmas issue of the St Stephen's Review which includes cartoons and satirical pieces about Lord Randolph Churchill, William Gladstone, [Robert, 3rd] Lord Salisbury, Charles Bradlaugh, and other political figures. Some of the cartoons are annotated with notes about the identity of those portrayed.

Letter from Lord Randolph Churchill (Jorresdal [Jordal, Norway]) to [Lady Randolph Churchill] including: his opinion that an address he gave in London had a favourable effect in the election; his anticipation that the Conservatives will remain in government for a considerable time; financial affairs; and his success at fishing.

Letter from WSC (Royal Military College, Sandhurst, [Camberley, Surrey]) to "Mamma" [Lady Randolph Churchill] in which he discusses arrangements for a dentist's appointment and comments that "Papa" [Lord Randolph Churchill] has not sent him his allowance and that [Elizabeth] Everest has not received a cheque.

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 thanks her for sending him a costume, discusses arrangements for her to visit him and asks her to send him money.

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 (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].