Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mummy" [Lady Randolph Churchill] complaining of toothache and requesting that she should send him money to travel to an appointment with the dentist as he has paid his debts and given up betting.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] informing her that his toothache has gone, asking after "poor Grandmamma Duchess" [Frances, Duchess of Marlborough] and requesting that she should send him money for subscriptions Annotated "Hurrah for Nunthorpe" [a racehorse which had won the Great Jubilee Stakes at Kempton Park races].

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] informing her that he has been in the "deuce of a row" for breaking factory windows and asking her to send him money as he is "absolutely 'oofless'".

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mummy"[Lady Randolph Churchill] in which he informs her that his [toothache] has got better, asks about the health of various animals and says that [Elizabeth] Everest has sent him a hamper.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he informs her that he has had his tooth taken out and asks her to send him money.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] asking her to meet him and to send him money to pay a "bicycle debt" and to repair [factory] windows which he had smashed.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mummy" [Lady Randolph Churchill] asking her to send him money.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he says that he was not disappointed at not seeing her on Saturday, that he hopes to be permitted to attend her concert and that he has copied a letter from [Lord Randolph Churchill] for "Jack" [John S Churchill].

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he entreats her to allow him to go to Lords cricket ground.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] concerning [James] Welldon's proposal that WSC should spend part of his holidays in France. WSC says that [Lord Randolph Churchill] considers the plan "utter nonsense" and argues that he should not be made to go to "a filthy den". In a postscript he comments "I feel less keen about the army every day. I think the church would suit me much better" and bids her to ask Count Kinsky about fireworks.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he asks her to write [concerning James Welldon's proposal that WSC should spend part of his holidays in France] and to send him some money, and reports that he has been made a Lance Corporal.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he says that he is looking forward to returning home and asks her to make arrangements for shooting at Banstead [Manor, Newmarket, Suffolk].

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he says that [James] Welldon would like her to write to him to explain why WSC did not return to school until Thursday and asks her not to mention the theatre in her letter to Welldon.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mummy" [Lady Randolph Churchill] informing her that he has settled down well and that he has been permitted to study Chemistry instead of German and asking her to send him money.

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he says that he enjoyed "Papa's" [Lord Randolph Churchill's] visit and that he is looking forward to the holidays. Envelope present.

Letter from WSC (Reverend James Welldon's, Harrow School [Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he says that Welldon is determined that WSC should get his remove and that he hopes that he will be allowed to take a holiday on his birthday. Envelope present.

Letter from WSC ([Harrow]) to "Mama" [Lady Randolph Churchill] describing the contents of an examination he has taken and his hopes that he has passed. He lists the essay questions which were set and comments on his luck that he had revised the map of New Zealand. Envelope present.

Telegram from WSC (Harrow School [Middlesex]) to [Elizabeth] Everest informing her that he is well and that he has secured his remove.

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he says that he was surprised that she visited him in such bad weather and suggests that she might like to come to see the assault at arms or the grand concert. Envelope present.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he apologises for not writing earlier as he has been busy and has been "on lines" for two half holidays and asks her to visit him. Envelope present.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mama" [Lady Randolph Churchill] in which he informs her that he has secured his remove, comments that he has become economical and asks her to sign an enclosure to confirm that he has had measles. Envelope present.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he says that he had not worked hard due to laziness and consequently had received a bad report. He says that her letter "cut me up very much" and explains that he had replied to a letter from "Papa" [Lord Randolph Churchill] but that it had not been posted by the Page and describes his hopes of passing examinations in Geography, French and English dictation and composition. Envelope present.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mamma" [Lady Randolph Churchill] describing the clothes that he has ordered which are illustrated with drawings and asking her to send him money. He encloses a fabric sample [CHAR 28/18/W41]. Envelope present.

Letter from WSC ([Banstead Manor, Newmarket, Suffolk]) to "Mamma" [Lady Randolph Churchill] informing her of his safe arrival, discussing activities he has planned and commenting that "Jack" [John S Churchill] sends her "14 pints of love and 26 brace of kisses". Envelope sealed with black wax.

Letter from WSC (Banstead Manor, Newmarket [Suffolk]) to "Mamma" [Lady Randolph Churchill] in which he says that he and "Jack" [John S Churchill] are enjoying themselves although he expresses his disappointment at not being allowed to shoot and describes [Lady Sarah Churchill, later Sarah Wilson] as being unpleasant towards him. Envelope present.