Illustrated card from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Papa" [Lord Randolph Churchill] in which he reproaches his father for not visiting him when he was in Brighton, describes visiting a museum and asks his father to send more copies of his autograph.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mama" [Lady Randolph Churchill] asking her not to forget to write to Miss Thomson to allow him to come home and reporting on his success in a gymnastic examination.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] describing the progress of the school play and asking her to come to give out the prizes.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mama" [Lady Randolph Churchill] in which he asks her to remain in Brighton after distributing the school prizes, rather than returning to London for a dinner party and includes the programme for the evening as "mice are not caught without cheese".

Letter from WSC ([29 & 30 Brunswick Road, Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] informing her of his safe return to school and asking about the contents of his school report.

Letter from "The Pussy Cat" [WSC] ([29 & 30 Brunswick Road, Hove, East Sussex]) to "Mummy" [Lady Randolph Churchill] wishing her a pleasant journey.

Letter from "Winny" [WSC] ([29 & 30 Brunswick Road, Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] in which he says that he is well but wants to return home.

Letter from "Winny" [WSC] ([29 & 30 Brunswick Road, Hove, East Sussex]) to "Mummy" [Lady Randolph Churchill] in which he says that he is occupied with the football team and reproaches her for not writing to him.

Letter from "Winny" [WSC] ([29 & 30 Brunswick Road, Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] in which he says that he is looking forward to receiving a letter from her and asks her to send his love to "Papa" [Lord Randolph Churchill].

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.