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.

Letter from "Winny" [WSC] (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] informing her of the progress of his school examinations.

Letter from "Jack" [John S Churchill] (Elstree School, Herts) to WSC, on the Harrow Fencing Cup.

Letter from "Jack" [John S Churchill] to WSC, on publication of letter from WSC in "The Harrovian".

Letter from "Jack" [John S Churchill] (Harrow School) to WSC, With little to report due to WSC's recent visit, commenting on WSC's good time in London.

Letter from Lord Randolph Churchill, 2 Connaught Place, London to WSC, thanks for letters containing news of Harrow, also commenting on the death of "poor Daisy" and sending postal order for 21s.

Letter from Lord Randolph Churchill, 2 Connaught Place, London to WSC, on the need for WSC to return to Harrow a week early to prepare for the Sandhurst entrance examination, with Lord Randolph's reminiscences about his final examinations at Oxford. Also commenting on the death of the Duke of Clarence "one Of the saddest events I have ever known".

Letter from Lord Randolph Churchill, 2 Connaught Place, London, to WSC, congratulations on WSC's success in the Harrow School Fencing competition. "I only hope fencing will not too much divert your attention from the Army Class.

Letter from WSC [letter signed "De Profundis"] to "The Harrovian" on the inadequacy of certain classrooms at Harrow School, recommending that new classrooms be built [copy].

Letter from Prince Alfred of Edinburgh to WSC, apologising for "hurting WSC's head, and hoping that he was making a " good recovery, and that "you have no ill feeling against me".

Letter from Prince Alfred of Edinburgh to WSC, offering sympathy on illness, and account of visit to The Mikado.

Letter from Jack Milbanke, (Eartham, Chichester) to WSC, congratulations on obtaining Remove [into the First Division of the Fourth Form at Harrow].

Letter from Jack Milbanke, Eartham, Chichester, to WSC, on WSC's troubles at Harrow, hunting, and on Milbanke's Commission in the Sussex Militia.