Letter from "W" [Elizabeth Everest], 2 Connaught Place, London, to WSC, family news.

Letter from "Woom" [Elizabeth Everest] to WSC, on Christmas celebrations at the Churchill's London home, 2 Connaught Place.

Letter from "Woom" [Elizabeth Everest], 2 Connaught Place, London, to WSC, thanks for Christmas presents, family news.

Letter from "Woom" [Elizabeth Everest], 50 Grosvenor Square, London, to WSC, complaining that WSC had not written to Lady Randolph.

Letter from "Woom E A E" [Elizabeth Everest], 5 Cranmer Road, Forest Gate, Essex, to WSC, family news.

Letter from "Woom" [Elizabeth Everest], 5 Cranmer Road, [Forest Gate] to WSC, on his toothache and his boils.

Letter from "Woom" [Elizabeth Everest], 5 Cranmer Road, [Forest Gate] to WSC, on his health.

Letter from "Woom" [Elizabeth Everest], St George's Vicarage, Barrow-in-Furness to WSC, advice on his health, and on her stay in Barrow.

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 Laura, Lady Wilton (later Lady Johnstone), Le Nid, Monte Carlo, to WSC, on the Sandhurst Entrance Examination.

Letter from John Milbanke, Depot, Royal Sussex Regiment, to WSC, on WSC's life at Harrow School, and success in the Army Preliminary Examination, and Milbanke's life in the Royal Sussex Regiment.

Letter from Charlotte Thomson to WSC, on Brunswick Road School, Brighton.

Letter from Maxwell McTaggart to WSC, on the Sandhurst Entrance Examination.

Letter from Louis Moriarty, Army Class Master, Harrow School, to WSC, on WSC's "very creditable" failure in the Sandhurst entrance examination. Stating that if he worked "earnestly and sensibly" he would pass in November.

Letter from Rev. James Welldon, Headmaster, Harrow School, to WSC, on his failure in the Sandhurst entrance examination. Urging him to work "not by fits and starts but with regular persistent industry". Commenting that the grammatical foundation of his language was so uncertain that he lost marks which other boys gained "You therefore have ground to make up as well as new ground to cover".

Letter from Louis Moriarty, Army Class Master, Harrow School, to WSC, listing the numbers of the Harrow candidates in the Sandhurst entrance examination.

Letter from Colonel John Brabazon to WSC, invitation to visit 4th Hussars at Aldershot, and to meet Captain Julian Byng, 10th Hussars [later Lord Byng of Vimy].

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, congratulations on obtaining Remove [into the First Division of the Fourth Form at Harrow], hoping that he would continue to work. Asking him to write at least twice a week.

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.