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 Lord Randolph Churchill (Cliveden, Maidenhead [Buckinghamshire]) to [Lady Randolph Churchill] discussing financial matters and asking her to be more careful; describing an expedition to Oxford with [Lady] Sarah [Churchill, later Sarah Wilson], WSC and "Jack" [John S Churchill] and "Jack's" first ride on his pony and discussing arrangements for her to come to Cliveden.

Letter from WSC (St George's School, Ascot [Berkshire]) to "Mama" [Lady Randolph Churchill] in which he reproaches her for not writing to him and asks her to visit on June 24 and to allow [Elizabeth] Everest and "Jack" [John S Churchill] to visit. Envelope present.

Letter from WSC ([29 & 30 Brunswick Road, Hove, East Sussex]) to "Oom" [Elizabeth Everest] in which he describes his recent illness, asks her to come and visit him with "Jack" [John S Churchill] and says that he is going to give "Mama" [Lady Randolph Churchill] a "lecture" for not writing to him.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Papa" [Lord Randolph Churchill] asking for [Lady Randolph Churchill's] address and saying that he would be "very proud" if his father would write to him.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Papa" [Lord Randolph Churchill] in which he says he cannot understand why his father did not visit him when he was in Brighton and asks for money for a stamp album.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Papa" [Lord Randolph Churchill] in which he says that he hopes that his father will be elected as MP for Birmingham [Central] and says that if Colonel Tottenham, the father of another school boy, is elected for Winchester, they may have a "supper".

Letter from WSC ([29 & 30 Brunswick Road, Hove, East Sussex]) to "Mummy" [Lady Randolph Churchill] in which he says that he hopes that she is not at risk from the London mobs and asks her to allow "Oom" [Elizabeth Everest] and "Jack" [John S Churchill] to remain in Brighton longer.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Papa" [Lord Randolph Churchill] thanking him for sending him stamps and autographs, commenting on a fire at 2 Connaught Place [London], reporting on his progress at school and wishing him success in his speech at Bradford [Yorkshire] "I hope you...cut the ground from under the feet of the Liberals".

Illustrated card from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Papa" [Lord Randolph Churchill] in which he reproaches his father for not visiting him when he was in Brighton, describes visiting a museum and asks his father to send more copies of his autograph.

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

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 Jack Milbanke (17 Cliveden Place, Eaton Square) to WSC, offering help, and to intercede with Lady Randolph Churchill if he could be of any use.

Letter from "Jack" John S Churchill (Banstead Manor, Newmarket) to WSC, on their "den" which was dirty inside, but had withstood the weather well, and on the health of the animals.

Letter from Lady Randolph Churchill, 2 Connaught Place, London, to WSC, on his "very bad" school report from Harrow Describing his work as an "insult to his intelligence", and contrasting him to his brother Jack "who comes out at the head of his class every week".

Letter from Lady Randolph Churchill, Banstead, to WSC, apologies for not visiting him at Harrow, and advising him not to sell his bicycle and buy a bulldog puppy "a dog is sometimes a nuisance".

Letter from Lady Randolph Churchill, Iwerne Minster House, Blandford, to WSC, on his school report "You must try & have a better one next term as Papa will be back & will expect glowing accounts of yr work." Also commenting on a day's hunting, and "cutting a lovely somersault" at the 3rd fence.

Letter from [Lady Randolph Churchill] to [Lord Randolph Churchill] in which she describes an evening with the de Mondys, reports that the baby [WSC] is better but sad that he is away and asks him to send her regards to [Lord] Blandford [later George, 8th Duke of Marlborough].

Letter from [Lady Randolph Churchill] to [Lord Randolph Churchill] in which she discusses household accounts and the servants; asks about the Hague [The Netherlands] and [Lord] Blandford [later George, 8th Duke of Marlborough] and reports that WSC is missing him.