Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] in which he expresses his disappointment at not being able to spend his holidays with her and asks whether Mr Best may be able to teach him and "Jack" [John S Churchill].

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Grandmama" [Frances, Duchess of Marlborough] informing her of his safe arrival and apologising for not writing previously.

Letter from WSC (Blenheim Palace) to "Papa" [Lord Randolph Churchill] in which he says that he hopes his father is getting better, that he has been picking primroses and that he has seen three "Indian children".

Letter from WSC (Blenheim Palace) to "Papa" [Lord Randolph Churchill] thanking him for his letter, and saying that he has been studying with [Frances, Duchess of Marlborough] who is going to London on the following day to see him and sending him and [Lady Randolph Churchill] "many kisses".

Letter from Lord Randolph Churchill (Banstead Manor, Newmarket [Suffolk]) to [Lady Randolph Churchill] reporting that [WSC and John S Churchill] have been good and that WSC rides well. He also relates his anger about arrangements for racing [his racehorse] Inverness and that WSC has made friends with the servants and is "full of local gossip".

Letter from Lord Randolph Churchill (Cliveden, Maidenhead [Buckinghamshire]) to [Lady Randolph Churchill] reporting his safe arrival at Cliveden; describing an evening spent at Moulton [Paddocks, Newmarket, Suffolk] where "Lady G" was amusing about her lovers and his success at the races at Windsor [Berkshire]; and commenting that [WSC and John S Churchill] are well and "permit us to lead a fairly tranquil existence".

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 ([Harrow School, Middlesex]) to "Papa" [Lord Randolph Churchill] in which he informs him that he has been congratulated about the "flukey filly" [the Abbesse, one of Lord Randolph Churchill's racehorses]; says that he would like to enter the army through the militia as he does not enjoy being in the army class at Harrow and reports comments he has heard about his father's parliamentary bill [concerning licensing regulations].

Letter from WSC ([Harrow School, Middlesex]) to "Papa" [Lord Randolph Churchill] in which he informs him that he is not able to sit his preliminary examination this term and that he has been celebrating the success of the Abbesse [one of Lord Randolph's racehorses].

Letter from WSC ([Banstead Manor, Newmarket, Suffolk]) to "Mummy" [Lady Randolph Churchill] describing the number of rabbits he has "slaughtered" and the cold weather.

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 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 ([Blenheim Palace]) to "Papa" [Lord Randolph Churchill] in which he says that he has been to the Lince with "Baby" [John S Churchill] where he picked hyacinths, and that he has seen a snake which [Elizabeth] Everest would not let him kill.

Drawing of WSC as a small child on a red sofa. Includes frame.

Letter from James Welldon ([Harrow School, Middlesex]) to Lady Randolph [Churchill] in which he discusses arrangements concerning WSC and an appointment with [Bernard] Minssen. He observes that WSC must work while he is staying with [Bernard] Minssen to improve his French, and urges that he should only be allowed to see limited numbers of English-speaking people and says that he is determined that WSC should be accepted by Sandhurst.

Letter from James Welldon (Harrow School [Middlesex]) to Lady Randolph [Churchill] in which he suggests that WSC should spend part of his holiday in France.

Letter from James Welldon (Harrow School [Middlesex]) to Lady Randolph [Churchill] suggesting that WSC should be sent to spend part of his holiday with Madame Elmering in Rouen, France and recommending that he should be urged to work hard to increase his chances of being accepted into Sandhurst.