Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he says that he is sorry that she could not visit him, asks her to allow [Elizabeth] Everest to bring him ornaments, details the "'oof'" [money] he has spent on furnishing his room and money which he owes, and asks her to send him a P[ost] O[ffice] O[rder] and to ask [James] Welldon to allow him to visit [John, 7th Duke of Marlborough].

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he expresses relief about the health of [John, 7th Duke of Marlborough], says that he is looking forward to seeing [Lord Randolph Churchill] and advises her not to make herself ill with worry.

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] complaining of toothache and informing her that he has secured his remove and become "Head of the Fags".

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 "Mummy" [Lady Randolph Churchill] in which he discusses purchasing a bull dog, asks her to make a doctor's appointment for him and to write to [James] Welldon to thank him for arranging private lessons for him.

Letter from WSC (Harrow on the Hill [Middlesex]) to "Mummy" [Lady Randolph Churchill] asking her to send him money and informing her that he is going to see "Jack" [John S Churchill].

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 (Harrow on the Hill [Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he explains that the money he had requested had been spent on journeys to [London] and defends his request to be sent ducks from Banstead [Manor, Newmarket, Suffolk] and asks her not to be "wrothful without cause".

Letter from WSC (Harrow on the Hill [Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he says that he has visited "Jack" [John S Churchill] and asks her to allow them to attend the wedding of [Lady] Sarah [Churchill, later Sarah Wilson to Gordon Wilson], not to send him to a French family for his holidays and to send him some "filthy lucre" [money].

Letter from WSC (Harrow on the Hill [Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he thanks her for sending him money, asks her to allow him to attend the wedding of [Lady Sarah Churchill, later Sarah Wilson to Gordon Wilson] and begs her not to make him spend his holidays with a "nasty, fusty and beastly" French family.

Letter from WSC (Harrow on the Hill [Middlesex]) to "Mamma" [Lady Randolph Churchill] informing her of his safe return, asking her to allow [Elizabeth] Everest and "Jack" [John S Churchill] to visit him, and commenting on his bad luck in being obliged to leave [the wedding of Lady Sarah Churchill, later Sarah Wilson to Gordon Wilson] when he was "making an impression on the pretty Miss Weaslet".

Letter from WSC (Harrow on the Hill [Middlesex]) to "Mamma" [Lady Randolph Churchill] asking her not to send him to Paris [France] before Christmas warning her that if she does "the holidays will be one continual battle".