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 "Winny" [WSC] ([29 & 30 Brunswick Road, Hove, East Sussex]) to "Womany" [Elizabeth Everest] informing her that he has settled down.

Part of a letter from WSC to [Lady Randolph Churchill] reporting that he was top of his form in a gymnastic examination and sending his love to other family members.

Dictation exercise by WSC corrected and marked.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] in which he details his marks for conduct and says that "Little Kim" [Lord Kimbolton, later 9th Duke of Manchester] is settling in well.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mama" [Lady Randolph Churchill] in which he says that he would like to see "Ruddygore", asks to be given a chess set and describes the characters in "The merry men of Sherwood forest" in which he plays Robin Hood.

Letter from "Winny" [WSC] (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] in which he describes the weather and a visit to the Marine Parade.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] in which he says that he hopes she is well and reports that he has had examinations in arithmetic and Euclid.

Letter from WSC (29 & 30 Brunswick [Road] Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] asking about her sea crossing and saying that he is looking forward to the holidays.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] in which he gives the dates of the Easter holidays, describes the weather and a dog given to Miss Thomson and says that he is looking forward to going to Birmingham.

Letter from WSC (29 & 30 Brunswick [Road] Brighton [Hove, East Sussex]) to "Mama" [Lady Randolph Churchill] in which he says that he is "blessed with that inestimable treasure i.e. 'Good Health'" and that he hopes to improve at his studies and at cricket.

Letter from "Winny" [WSC] (29 & 30 Brunswick Road Brighton [Hove, East Sussex]) to "Mama" [Lady Randolph Churchill] in which he says that he has been suffering from a bad cough and expresses concern about [Elizabeth] Everest and "Jack" [John S Churchill].

Letter from "Winny" [WSC] (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mama" [Lady Randolph Churchill] thanking her for her "epistle" and reporting that he has seen [Frances, Duchess of Marlborough].

Letter from "Winny" [WSC] ([29 & 30 Brunswick Road, Hove, East Sussex]) to "Mama" [Lady Randolph Churchill] discussing arrangements to see her on the following Monday. Envelope present.

Letter from "Winny" [WSC] (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] discussing the popularity of the Primrose League at school and asking whether he might join the London branch.

Letter from "Winny" [WSC] (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] discussing a cricket match between Gloucestershire and Sussex at which W G Grace is playing.

Letter from "Winny" [WSC] (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] in which he says that he has visited the swimming baths and asks her to send him autographs.

Letter from "Winny" [WSC] ([29 & 30 Brunswick Road, Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] in which he says that Miss Thomson thinks that he should not return home to attend the Jubilee and asks her to write to persuade her to the contrary, commenting "I am in a ferment about coming home".

Letter from "Winny" [WSC] (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] begging her to write to Miss Thomson to persuade her to allow him to attend the Jubilee and including his suggestions for the content of her letter Illustrated with drawings of soldiers and a face. Envelope present.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] informing her of his safe arrival, asking her not to let his bad behaviour influence his summer holidays and reporting that he has made good progress with Euclid.

Letter from "Winny" [WSC] (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] in which he reports that he is doing well in Euclid, Greek, Latin and swimming and asks her to send him "Jess".

Letter from "Winny" [WSC] (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] thanking her for her letter and reporting that he is going to Bramber [West Sussex] for the "annual treat" and that his Greek has improved and he has made progress with Euclid.

Letter from "Winny" [WSC] ([29 & 30 Brunswick Road, Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] asking for money, books and autographs and saying that he hopes she is not intending to employ a tutor and "make my holiday miserable".

Letter from "Winny" [WSC] (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] in which he says that he is looking forward to his holidays and asks whether "Bertie" Roose may accompany him and requests books, autographs and money.

Letter from "Winny" [WSC] ([29 & 30 Brunswick Road, Hove, East Sussex]) to "Mummy" [Lady Randolph Churchill] thanking her for sending him autographs and money, commenting that he "did not enjoy the letter quite so much" and asking her not to force him to work during his holidays.