Letter from Lord Randolph Churchill, 2 Connaught Place, London to WSC, complaining about WSC's spending "I think you have got through about £10 this term. This cannot last, & if you are not more careful should you get into the army six months of it will see you in the Bankruptcy Court".

Letter from Lord Randolph Churchill, 50 Grosvenor Square, London to WSC and John S Churchill, on Lady Randolph's illness and on the death of his brother-in-law, the Duke of Roxburgh.

Letter from Lord Randolph Churchill, 50 Grosvenor Square, London to WSC, on WSC's visit to London and on Lady Randolph's illness.

Letter from Lord Randolph Churchill, Le Nid, Monte Carlo, Monaco, to WSC, urging him to work hard at Sandhurst - to "keep the standard up & keep raising"...Pull yourself together & keep yourself well abreast & even ahead of those you are competing with..Keep down the smoking, keep down the drink & go to bed as early as you can" With postscript suggesting that he should substitute "father" for "papa" in future letters.

Letter from Lord Randolph Churchill, 50 Grosvenor Square, London, to WSC, on the success of WSC's riding instruction with Captain C H Burt, and recommending that he should visit Lord Randolph's dentist, Pritchard, of 9 Albemarle St., London.

Telegram from Lord Randolph Churchill to WSC, asking WSC not to come up to London as Lord and Lady Randolph were going to Tring.

Letter from Lord Randolph Churchill, 50 Grosvenor Square, London, to WSC, complaining about WSC's frequent visits to London from Sandhurst, forbidding him to come to London more than once a month, and encouraging him to study at weekends.

Letter from Lord Randolph Churchill, 50 Grosvenor Square, to WSC, on WSC's visit to Colonel John Brabazon, 4th Hussars, at Aldershot, and his work at Sandhurst, telling him "not to trouble any more about the watch", [which WSC had damaged] as the rough work of Sandhurst was not suitable for a watch made by Dent. Also advising him not to "attend to moneylenders," put their letters into the waste paper basket".

Letter from Lord Randolph Churchill, 50 Grosvenor Square, London, to WSC, sending cheque to cover WSC's allowance.

Letter from Lord Randolph Churchill, 50 Grosvenor Square, To WSC, on visit to Lord Roberts at Grove Park, also on forthcoming visit of the Prince of Wales to Harrow School. Advising WSC to take care with his diet, "Eating fast, as you do is a fertile source of indigestion & heated blood, producing boils". Also advising him to address him as "Dear Father" rather than "Papa" in future letters.

Letter from Lord Randolph Churchill, 50 Grosvenor Square, to WSC, criticising him for addressing him as "Papa" rather than "Father" in letters "This is idiotic".

Letter from Lord Randolph Churchill to WSC, on the state of WSC's finances, and his "pedantic and overgrown schoolboy style of letter writing, and complaining about his use of a typewriter "an objectionable machine calculated to spoil your handwriting.

Letter from Lord Randolph Churchill, Bar Harbour Malvern Hotel, Maine, to WSC, on Lord and Lady Randolph's visit to the United States and Canada, and on WSC's proposed visit to Germany.

Letter from Lord Randolph Churchill, Hotel del Monte, California, to WSC, on WSC's desire to join the cavalry rather than the 60th Rifles, pointing out that the Duke of Cambridge would be extremely angry, and that he would also oppose the change strongly, also on Lord and Lady Randolph's visit to the United States, and forthcoming Voyage to Japan.

Letter from Frances, Duchess of Marlborough, [WSC's grandmother], 50 Grosvenor Square, to WSC, family news, visit to the Gaiety Theatre to see Ruy Blas by A C Torr, picture of Lord Randolph Churchill in "Punch", and Lord Randolph's Temperance Bill.

Letter from Frances, Duchess of Marlborough, Woodlands, Uxbridge, to WSC, family news.

Letter from Frances, Duchess of Marlborough, Ramsey Abbey, Huntingdon to WSC, his success in the Sandhurst Entrance Examination, Lord and Lady Randolph's visit to Germany, and other family news.

Letter from Clara Hall Jerome [WSC's grandmother], 53 Seymour Street, Portman Square, to WSC, on his finances, and his success in the Sandhurst Entrance examination.

Letter from Frances, Duchess of Marlborough, Canford Manor, Wimborne, Dorset, to WSC, family news.

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

Letter from "Woom" [Elizabeth Everest] [2 Connaught Place, London] to WSC, family news and advice, hoping to visit him shortly at Harrow.

Letter from "Woom" [Elizabeth Everest], Banstead, to WSC, on his finances, and family news.

Letter from "Woom" [Elizabeth Everest], Banstead, to WSC, family news.