Letter from WSC ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he says that he is enjoying being in [James] Welldon's house and asks her to send him money and to visit him.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he says that he is well and describes his success at a rifle range.

Letter from WSC ([Harrow School, Middlesex]) to "Mama" [Lady Randolph Churchill] in which he reports that he has fallen on the back of his head and asks her to come and visit him.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] thanking her for allowing "Woom" [Elizabeth Everest] to visit him although he says that he was disappointed at not seeing her [Lady Randolph] and asks her to visit him.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] thanking her for allowing "Woom" [Elizabeth Everest] visit him and saying that the doctor has advised him that he should rest and that he would like to come home.

Letter from "Winny" [WSC] ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he describes his bicycle accident, asks her to visit him and to allow [Elizabeth] Everest to visit as he is bored.

Letter from WSC ([Harrow School, Middlesex]) to [Lady Randolph Churchill] asking her to send him money.

Letter from "Winny" [WSC] ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] describing the extent of an outbreak of measles at school and asking her to allow him to return home, commenting "I should have imagined that as 300 mamas & 300 papas like to have their 'offsprings' home you would like to have me".

Letter from WSC to "Mamma" [Lady Randolph Churchill] informing her that he and "Jack" [John S Churchill] have arrived safely and that "Jack" felt tired and attributed it to a fishbone which he had swallowed six months previously and describing a visit to a landslip.

Card from WSC (Harrow on the Hill [Middlesex]) to "Mama" [Lady Randolph Churchill] informing her of his safe arrival and that he is sharing a room with Count Eric Steenbock [Stenbock, the son of a Swedish-Norwegian Minister] and is not spending his money rashly.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he says that he does not need money, commenting "my Excheqeur is quite full at the moment" and asks her not to go to Mashonaland [Rhodesia, later Zimbabwe].

Part of a letter from WSC ([Harrow School, Middlesex]) to [Lady Randolph Churchill] asking her to come and speak to [James] Welldon and "stick up for" him.

Letter from WSC ([Harrow School, Middlesex] on the notepaper of Lexden House, Colchester) to "Mummy" [Lady Randolph Churchill] asking her to come and visit him.

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 (The Head Master's, Harrow School [Middlesex]) to "Papa" [Lord Randolph Churchill] in which he says that he is getting on well and that "Mamma" [Lady Randolph Churchill] sent him some oranges from Monte Carlo [Monaco] and that he has received a letter from "Jack" [John S Churchill] about Elstree [Hertfordshire].

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] informing her that he has secured his remove and has started learning German and commenting on the success of the "Habbesse" [the Abbesse, one of Lord Randolph Churchill's racehorses].

Letter from WSC ([Harrow School, Middlesex]) to "Papa" [Lord Randolph Churchill] in which he informs him that he has been congratulated about the "flukey filly" [the Abbesse, one of Lord Randolph Churchill's racehorses]; says that he would like to enter the army through the militia as he does not enjoy being in the army class at Harrow and reports comments he has heard about his father's parliamentary bill [concerning licensing regulations].

Letter from WSC ([Harrow School, Middlesex]) to "Papa" [Lord Randolph Churchill] in which he informs him that he is not able to sit his preliminary examination this term and that he has been celebrating the success of the Abbesse [one of Lord Randolph's racehorses].

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he expresses approval for a play at the Adelphi theatre [London] called "An English Rose" [by George Sims and Robert Buchanan]. Illustrated with a drawing of a Harrow schoolboy surrounded by luggage.

Letter from "Winny" [WSC] (The Head Master's, Harrow School [Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he asks her to write to him concerning patterns and to send him some "oof" [money].

Letter from WSC ([Harrow School, Middlesex]) to "Papa" [Lord Randolph Churchill] thanking him for sending him game, reporting that the army class master thinks that he will pass his examination and that he has been forced to wear a truss and commenting on the Eccles [Lancashire] by election [in which a Conservative lost the seat to a Liberal].

Letter from WSC ([Harrow School, Middlesex]) to "Mama" [Lady Randolph Churchill] in which he says that he has received no information about her or Grandpapa [John, 7th Duke of Marlborough] and asks her to write to him by return of post and send him money.

Letter from WSC ([Harrow School, Middlesex]) to "Mama" [Lady Randolph Churchill] in which he says that he is getting on well and asks her to send him money for a visit to see "Jack" [John S Churchill].

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mamma" [Lady Randolph Churchill] asking her to make arrangements for someone to attend speech day.

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.