Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] asking her to send him money for subscriptions as "you promised I should not be different to others" and informing her of his position in class.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he describes his progress at school, (including in mathematics in which he is studying stocks), a "Sale by Auction" and a paper chase and says that he hopes she is enjoying her "spree on the continong [continent]".

Letter from WSC ([Harrow School, Middlesex]) to "Papa" [Lord Randolph Churchill] asking him to write to [James] Welldon concerning his school house and describing a "sham fight" with other schools.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he expresses his disappointment that she did not come to visit him and asks her to visit him on the next day.

Letter from WSC (Reverend [James] Welldon's, Harrow School [Middlesex]) to "Papa" [Lord Randolph Churchill] discussing arrangements for speech day and the areas of the school which he could show his father.

Letter from WSC (Reverend [James] Welldon's, Harrow School [Middlesex]) to "Mamma" [Lady Randolph Churchill] asking her to persuade [Lord Randolph Churchill] to attend speech day and to allow [Elizabeth] Everest to visit him.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] reproaching her for forgetting him, asking her to send him money, to arrange an appointment with the oculist, and to sign a form permitting him to begin fencing.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Papa" [Lord Randolph Churchill] informing his father that he has secured his remove.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mama" [Lady Randolph Churchill] informing her that he has secured his remove and thanking her for sending him oranges.

Letter from "Winny" [WSC] (The Head Master's, Harrow School [Middlesex]) to "Woom" [Elizabeth Everest] informing her of his safe arrival and detailing the clothes he has ordered.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mamma" [Lady Randolph Churchill] promising to give up smoking for six months, reporting that "Jack" [John S Churchill] is "very low" and describing the decoration of his room. Illustrated with drawings of Harrow school boys and uniform.

Letter from "Winny" [WSC] ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he explains that he has been working very hard and details his hopes for success in individual subjects and comments that he is "afraid some enemy hath sown tares in your mind".

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 ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] asking her to reimburse him for money spent on a visit to the doctor's and detailing what he has spent.

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 "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] 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.

Essay by WSC on the physical geography and history of Palestine [Israel] and its people in the time of John the Baptist (25 BC to AD 1).

Letter from Lord Randolph Churchill (Makerstoun House, Kelso [Roxburghshire]) to Jennie [Lady Randolph Churchill] including: the success of a racehorse called Renard; the people he has met; comments on the British government's policy on Uganda and a visit to Harrow to see WSC and John S Churchill at which [James] Welldon had discussed the likelihood that WSC would pass his next examination.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lord Randolph Churchill] in which he expresses his pleasure that he is going to Harrow [School] rather than Winchester [School]; discusses his progress with Euclid, arithmetic and Greek; reports that he is to play roles in plays by Moliere and Aristophanes and says that he wished that his father could attend the distribution of prizes.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mama" [Lady Randolph Churchill] in which he reports on his progress with Greek, Euclid and Latin.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] in which he says that he would like her and [Lord Randolph Churchill] to attend the distribution of prizes, discusses his birthday party and the future examinations, and asks for more of her autographs as "there is rather a demand for them here".

Letter from "Winny" [WSC] ([29 & 30 Brunswick Road, Hove, East Sussex]) to "Mama" [Lady Randolph Churchill] thanking her for a P[ostal] O[rder] and detailing his examination marks and positions. Envelope present.

Part of a letter from [WSC] (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] in which he reports that he has begun to learn Greek verbs ending in "mi", describes a visit to the theatre with [Lady Wimborne, earlier Cornelia, Lady Guest and Lady Cornelia Churchill] and hints that he would like to be given an illustrated history of the American [civil] war as a birthday present.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] in which he says that he intends to write to [Lord Randolph Churchill] and that he is rehearsing "the Greek play" ["The Knights" by Aristophanes].