Letter from Lady Randolph Churchill, 2 Connaught Place, London, to WSC, on the illness of Leonard Jerome.

Letter from Lady Randolph Churchill, Banstead, to WSC, on his toothache, advising him to brush his teeth more frequently, also on the Newmarket races.

Letter from Lady Randolph Churchill, Banstead, to WSC, on his toothache, the Duchess of Marlborough's illness and the Newmarket races.

Letter from Lady Randolph Churchill, Oakley Court, Windsor, to WSC, apologies for not visiting him at Harrow, and hoping to see him the following week.

Letter from Lady Randolph Churchill to WSC, on his financial situation.

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, Banstead, to WSC, sending £1 and complaining about the state of his finances, also on his toothache, complaining that he had had another tooth out ".

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, 50 Grosvenor Square, London, to WSC, asking him to write, and criticising his new hat.

Letter from Lady Randolph Churchill, Sunningdale, to WSC, on her visit to the Ascot races, and on the Sandhurst entrance examination.

Letter from Lady Randolph Churchill, Kissingen, to WSC, on his success in the Sandhurst entrance examination, and his father's anger that he failed to obtain an Infantry cadetship, also on her visit to Germany and meeting with Bismarck.

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] (Elstree School, Herts) to WSC, on activities at school.

Letter from "Jack" [John S Churchill] (Elstree School, Herts) to WSC, on WSC's visit to Elstree.

Letter from "Jack" John S Churchill to WSC, (Elstree School) on WSC's visit to Elstree, contains sketch of cricket match and "white pony".

Letter from "Jack" John S Churchill (Elstree School) to WSC, asking WSC to send stamp book, and commenting on horse racing.

Letter from "Jack" John S Churchill to WSC, on the result of The Derby, and asking him to send stamp book.

Letter from "Jack" John S Churchill to WSC, on Jack's illness.

Letter from "Jack" John S Churchill (Elstree School) to WSC, on WSC's visit to the Eton v. Harrow cricket match at Lord's and on Jack's new pony.

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 "Jack" John S Churchill to WSC, on construction of a hammock.

Letter from "Jack" John S Churchill to WSC, on disappointment that WSC did not visit him at Elstree.

Letter from "Jack" [John S Churchill] (Elstree School) to WSC, account of meeting of hunt at Elstree, with sketches of huntsman and hounds.

Letter from "Jack" [John S Churchill] (Elstree School) to WSC, birthday greetings.

Letter from "Jack" John S Churchill (Canford Manor, Wimborne, [Dorset]) to WSC, on Jack's visit to Canford, with sketch of Lord Randolph Churchill "looking very well, but with a horrid beard".