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".

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, on WSC's failure in the Sandhurst entrance examination.

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 "Jack" John S Churchill to WSC, on the state of Jack's finances "I am bankrupt".

Letter from "Jack" [John S Churchill] (Harrow School) to WSC, school news, regretting that WSC would not be visiting, and commenting on report of speech by Lord Randolph Churchill in The Times.

Letter from "Woom" [Elizabeth Everest], 15 Crouch Hill, London to WSC, on her health and her finances, thanking him for sending £2 10s, and offering sympathy on the illness of Clara Hall Jerome [WSC's grandmother]. Advising him against steeplechasing "It is a dangerous pastime, but I suppose you are expected to do it".

Letter from Laura, Lady Wilton (later Lady Johnstone), Le Nid, Monte Carlo, to WSC, on Lord Randolph Churchill's health, and the death of George, 8th Duke of Marlborough.

Letter from Frances, Duchess of Marlborough, 50 Grosvenor Square, London, to WSC, granting him an allowance of £20 per month.

Letter from Lady Randolph Churchill, 2 Connaught Place, to WSC, asking for letter "I suppose when yr exchequer is at a low ebb I shall have the pleasure of hearing from you".

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, 21 Connaught Place, London to WSC, apologies for not being able to visit him at Harrow, also commenting that she was hoping to get Lord Randolph Churchill to "sacrifice that terrible beard", without success.

Letter from Lady Randolph Churchill, 2 Connaught Place, London, to WSC, on the illness of Leonard Jerome, [WSC's grandfather].

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.