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 Lord Randolph Churchill (Blenheim Palace) to [Lady Randolph Churchill] discussing shooting with [Lord] Fellowes [later 2nd Lord De Ramsey] and financial affairs.

Letter from Lord Randolph Churchill (Le Grand Hotel, Monte Carlo [Monaco]) to [Lady Randolph Churchill] relating the names of those he entertained at a dinner the previous evening, enclosing a letter [not present] from [Albert Edward, Prince of Wales],and discussing financial affairs and his lack of success at gambling.

Letter from Lord Randolph Churchill (Royal Station Hotel, York) to [Lady Randolph Churchill] in which he tells her that he is down o300 through losses at the races; discusses the possibility that Sir [?] Jatton may buy his racehorse the Abbesse for o3,000 and enclosing a bill [not present] for WSC.

Letter from Lord Randolph Churchill (2 Connaught Place [London]) to [Lady Randolph Churchill] in which he discusses financial difficulties and issues relating to domestic servants and reports that [Albert Edward, Prince of Wales] has invited him to dinner to meet "Harry" [Henry] Chaplin.

Letter from Lord Randolph Churchill (Cliveden, Maidenhead [Buckinghamshire]) to [Lady Randolph Churchill] discussing financial matters and asking her to be more careful; describing an expedition to Oxford with [Lady] Sarah [Churchill, later Sarah Wilson], WSC and "Jack" [John S Churchill] and "Jack's" first ride on his pony and discussing arrangements for her to come to Cliveden.

Letter from Lord Randolph Churchill ("In Camp", Fort Tuli [Rhodesia]) to [Lady Randolph Churchill] in which he describes his journey and living conditions, comments on the success of the expedition, outlines his plans for game hunting, and speculates on the effect of his letters to the Daily Graphic.

Letter from Lord Randolph Churchill (Fort Salisbury [Rhodesia]) to [Lady Randolph Churchill] in which he reports the lack of opportunity for speculating [for gold]; discusses his plans to meet the rest of the expedition and to return to England; anticipates [Cecil] Rhodes' anger at the mismanagement of the company's affairs and encloses a report [not present] for "Natty" [1st Lord Rothschild].

Letter from WSC (29 [& 30] Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] in which he asks for money as he has been "very extravagant" and has bought stamps and a stamp book.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] asking for a postal order of 10 shillings, relating the success of the second run of the school play and discussing arrangements for his return (which include a maid being turned out of his room).

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 WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mama" [Lady Randolph Churchill] asking her whether she will allow him to learn the violincello instead of the piano, speculating on the Conservatives electoral prospects and asking for money as he is "bankrupt".

Letter from "Winny" [WSC] (Prospects House, Skegness [Lincolnshire]) to "Mamma" [Lady Randolph Churchill] apologising for not writing previously and asking for money. Annotated with a note in the hand of Elizabeth Everest that "Master Winston" is continually requesting money which he wastes and advising that he should not be given any more money. Envelope present.

Letter from Lumley & Lumley, Solicitors, to WSC, on his income tax return.

Letter from Lumley & Lumley, Solicitors, London to WSC on his accounts.

Letter from Lumley & Lumley (Solicitors), 37 Conduit Street London, to WSC, on his proposal to borrow £3,500 from an insurance company on his reversionary interest under the will of his grandfather, the 7th Duke of Marlborough.

WSC's Bank Pass Book, for "Separate Account" with Cox & Co, Bankers, Pall Mall, London.

WSC's Bank Pass Book, Cox & Co., Pall Mall, London, [only one page of entries, remainder cut out].

WSC's Bank Pass Book, Cox & Co., Pall Mall, London [blank, all entries cut out].

Letter from Lord Randolph Churchill, 2 Connaught Place, London to WSC, complaining about WSC's spending "I think you have got through about £10 this term. This cannot last, & if you are not more careful should you get into the army six months of it will see you in the Bankruptcy Court".

Letter from Lord Randolph Churchill to WSC, on the state of WSC's finances, and his "pedantic and overgrown schoolboy style of letter writing, and complaining about his use of a typewriter "an objectionable machine calculated to spoil your handwriting.