Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] asking her to send him a postal order and discussing the start of examinations and arrangements for his return home.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] in which he reports that he has been unable to cash a postal order, describes an agricultural show and asks her to visit him.

Letter from "Winny" [WSC] (29 & 30 Brunswick Road [Hove, East Sussex]) to "Mama" [Lady Randolph Churchill] enclosing a photograph [not present] of himself and asking for money.

Letter from Lord Randolph Churchill (Le Nid [Monte Carlo, Monaco]) to [Lady Randolph Churchill] describing a trip to Nice [France] and the people he has met who include "Ronny" [Ronald] Greville and attempts by the Duchess of Montrose to "take the Nid by storm". He also discusses WSC's riding expenses and asks her to draw WSC's attention to "expressions of authority".

Letter from WSC ([Harrow School, Middlesex] on the notepaper of Banstead Manor, Newmarket) to "Mamma" [Lady Randolph Churchill] in which he apologises that he has not had the time to write as he has been busy with the "assault at arms", informs her that he is depressed that the examinations have finished and encloses an account of his necessary end of term expenses. Envelope present which includes a note "Mind and come on Thursday and slang me and kiss me Mummy".

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] asking her to come and visit him and informing her that he does not have sufficient money to pay his subscriptions.

Letter from WSC ([Harrow School, Middlesex]) to [Lady Randolph Churchill] asking her to send him money.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he says that he does not need money, commenting "my Excheqeur is quite full at the moment" and asks her not to go to Mashonaland [Rhodesia, later Zimbabwe].

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.

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].

Letter from WSC (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] discussing financial affairs and his search for a charger; saying that he had made friends and that Dudley Marjoribanks [later 3rd Lord Tweedmouth] has been sent to Canada because of an "inconvenient desire" for an actress.