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 (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] describing the death of [Elizabeth] Everest from peritonitis. He says that he employed a nurse and that he thinks that his visit "made her die happy" and that he visited "Jack" [John S Churchill] and discusses [Elizabeth Everest's] importance to him and Jack.

Letter from WSC (4th Hussars, Aldershot [Hampshire]) to "Mamma" [Lady Randolph Churchill] describing the funeral of [Elizabeth] Everest and his sadness at her death. He says that he is looking forward to the time that he has a home, reports that he is "getting on extraordinarily well" and comments on the stigma attached to those who are forced to leave a regiment through unpopularity.

Letter from WSC (Harrow on the Hill [Middlesex]) to "Mamma" [Lady Randolph Churchill] asking her to send his Preliminary [Examination] certificate to the military secretary as soon as possible.

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he says that he has settled down and that his room is "simply magnificent", informs her that he has secured his remove and that "Jack" [John S Churchill] "is getting on capitally".

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] asking her to attend Founders' day, reporting that he has seen Mrs [Norah] Stirling, [Reginald Stirling] and [Nathaniel] Rothschild and that "Jack" [John S Churchill] is getting on well.

Letter from WSC ([Harrow School, Middlesex] on the notepaper of Banstead Manor, Newmarket, Suffolk) to "Mamma" [Lady Randolph Churchill] in which he says that he has arrived safely, that he has written to "Papa" [Lord Randolph Churchill] who he hopes will not continue to be angry and that he hopes that she will feel better soon.

Letter from WSC ([Harrow School, Middlesex]) to Leonie [Leslie, formerly Leonie Jerome] in which he says that he has arrived safely, asks her whether she liked Drury Lane and says that "Jack" [John S Churchill] is well.

Letter from WSC ([Harrow School, Middlesex] on the notepaper of Banstead Manor, Newmarket) to "Mamma" [Lady Randolph Churchill] asking her to send a telegram to ensure that "Jack" [John S Churchill] will be able to have a day's leave.

Letter from WSC ([Harrow School, Middlesex] on the notepaper of Banstead Manor, Newmarket) to "Mamma" [Lady Randolph Churchill] in which he says that he has arrived safely, hopes that she is feeling better and encloses a form which he asks her to sign permitting him to have a new suit and to have photographs taken.

Letter from WSC ([Harrow School, Middlesex] on the notepaper of Banstead Manor, Newmarket) to "Mamma" [Lady Randolph Churchill] in which he apologises that he has not had the time to write as he has been busy with the "assault at arms", informs her that he is depressed that the examinations have finished and encloses an account of his necessary end of term expenses. Envelope present which includes a note "Mind and come on Thursday and slang me and kiss me Mummy".

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] asking her to come and visit him on Thursday and suggesting that they should go to the King's Head for lunch. The letter "M" at the start of the letter is composed of an illustration depicting a boy kicking a football.

Letter from WSC ([29 & 30 Brunswick Road, Hove, East Sussex]) to "Mama" [Lady Randolph Churchill] in which he details the terms under which he would be prepared to have a tutor during the holidays (including "That I don't do a stoke of work").

Letter from WSC ([29 & 30 Brunswick Road, Hove, East Sussex]) to "Mama" [Lady Randolph Churchill] responding to the news that "Mr Pest" [James Best] is to be his tutor during the holidays and promising to behave well provided that he is not made to work.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he informs her that he has joined the [army] corps, describes a mock battle with Haileybury school at Rickmansworth [Hertfordshire] and asks her and [Lord Randolph Churchill] to come and visit him. Illustrated with a plan of the battlefield.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] asking her to come and visit him and informing her that he does not have sufficient money to pay his subscriptions.

Essay by WSC on the physical geography and history of Palestine [Israel] and its people in the time of John the Baptist (25 BC to AD 1).

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] informing her that he is happy and is enjoying himself and asking her to visit him.

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] expressing his regret that she could not visit him, informing her that he is considered one of the best trebles in the choir, and asking her to allow [Elizabeth] Everest to bring him some money.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] informing her of his progress in the rifle drill and asking her to come and visit him. Includes illustration of soldiers and a cannon on the dorse.

Letter from WSC ([Harrow School, Middlesex]) to "Mama" [Lady Randolph Churchill] in which he apologises for not writing to her, reports that he has learnt 1,000 words of Macaulay and hopes that he will be awarded a "copy", a prize for English History.

Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he describes the clothes he would like to wear when collecting a school prize and asks her to allow [Elizabeth] Everest to bring them to him and to help him pack.

Letter from WSC ([Harrow School, Middlesex]) to [Lady Randolph Churchill] thanking her for allowing "Jack" [John S Churchill] and [Elizabeth] Everest to visit him and asking her to visit him and bring him a hamper.

Letter from WSC ([Harrow School, Middlesex]) to [Lady Randolph Churchill] expressing his pleasure that she is coming to visit him and promising her that he will be "specially got up for the occasion".