Letter from WSC (Hotel Continental, Milan [Italy]) to "Mama" [Lady Randolph Churchill] in which he expresses his disappointment at [Lord Randolph Churchill's] displeasure with him over his results in the [entrance] examination [for Sandhurst] after his hard work. He discusses his marks in individual subjects and says that he has a chance to alter his father's opinion of him.

Letter from WSC (Hotel Couronne & Poste [?Brigue, Switzerland]) to "Mamma" [Lady Randolph Churchill] in which he says that he is looking forward to going to Sandhurst and that his French is impressive, objects to her comment that he has written "a scrap" [short letter] to "Grandmamma" [Frances, Duchess of Marlborough], expresses his determination to work hard at Sandhurst and asks her to suggest to [Lord Randolph Churchill] that he should be given an allowance.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he says that he is getting on well and will sit his preliminary examination for Sandhurst in June, and asks to be allowed to do additional drawing classes and to continue fencing.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he expresses pleasure that he is not going abroad for his holidays, describes arrangements for a camp and asks her to give him money and to buy him a pair of butcher boots. He encloses the camp regulations [not present] and suggests that she might approach officers at Aldershot [Hampshire] to introduce themselves to him.

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 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 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".