Letter from WSC (Reverend James Welldon's, Harrow School [Middlesex]) to "Mamma" [Lady Randolph Churchill] in which he says that he is not "off reports" and that he hopes that she will visit him on his birthday. Envelope at CHAR 28/18/27.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he describes skating on "Ducker" [the swimming pool at Harrow], reports that he has been congratulated [?on passing the Preliminary examination for the army] and asks her to visit him. Envelope present.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] informing her that he is "all right" although is suffering from a cough. Envelope present.

Letter from WSC ([Harrow School, Middlesex]) to "Mummy" [Lady Randolph Churchill] in which he expresses relief that "Grandpapa" [John, 7th Duke of Marlborough] has reached Brighton [East Sussex] and asks her to visit him as he has been "disappointed so many times about your coming". Envelope present.

Letter from WSC (The Head Master's, Harrow School [Middlesex]) to "Mummy" [Lady Randolph Churchill] asking about the health of "Grandpapa" [John, 7th Duke of Marlborough] and requesting that [Elizabeth] Everest should make him an appointment with [Sir William] MacCormac as his leg is painful. Envelope present.

Part of a letter from [WSC] ([Harrow School, Middlesex]) to "Mamma" [Lady Randolph Churchill] asking her to speak to [James] Welldon about taking him "off reports" as he has received satisfactory reports and explains that he is unhappy, commenting "It's all very well for monitors & cricket captains but it is quite a different thing for fourth form boys".

Letter from WSC ([Versailles, France]) to "Mummy" [Lady Randolph Churchill] describing his journey to France, the soldiers he had seen in Versailles and a visit to the "Bon Marche" in Paris. He says that he would like to visit Baron [Moritz] Hirsch and that he almost wrote a letter which would have been "painful" to her due to his "fatigue, the passage, the strange food, the cold, home sickness..." The letter contains several passages and phrases in French.

Letter from WSC ([Versailles, France]) to "Mummy" [Lady Randolph Churchill] thanking her for her telegram, describing riding with [Bernard Minssen] and [Minssen's] mother's approval of his progress in French. The letter contains several passages and phrases in French.

Letter from WSC ([Versailles, France]) to "Papa" [Lord Randolph Churchill] expressing relief at the news that his father has returned safely, describing meetings with Baron [Moritz] Hirsch and [Marquis de] Breteuil and asking him to allow him an extra week's holiday so that he can see "Jack" [John S Churchill].

Letter from WSC ([Brighton, East Sussex]) to "Mamma" [Lady Randolph Churchill] describing his stay with Aunt Lily [Lilian, Duchess of Marlborough, later Lady William Beresford] during which he has met [Arthur] Balfour and Sir George Wombwell. Signed typescript.

Letter from Lord Randolph Churchill (Barton Lodge, Steeple-Aston, Oxfordshire) to [Lady Randolph Churchill] including: the trial for a case of attempted murder at Woodstock [Oxfordshire]; his intention to return to Ireland for Christmas; and his concern over WSC's health.

Letter from Lord Randolph Churchill to [Lady Randolph Churchill] including: advice about whether she should go to Sandown [Isle of Wight]; the eagerness of [John, 7th Duke of Marlborough] that the quarrel between Lord Randolph and Cornelia [Lady Guest, later Lady Wimborne, earlier Lady Cornelia Churchill] should be resolved; the time of his arrival in London and his pleasure at receiving "such flourishing accounts" of WSC.

Letter from Lord Randolph Churchill to [Lady Randolph Churchill] thanking her for her letter and describing the "Ruin" as "out of order". He expresses the hope that [Elizabeth] Everest's friends are "respectable" and asks [Lady Randolph] to instruct [Elizabeth Everest] not to allow WSC to play with other children, and says that he is feeling better.

Letter from Lord Randolph Churchill to [Lady Randolph Churchill] including his lack of success at fishing and a request that she give orders for WSC's hair to be cut short.

Letter from Lord Randolph Churchill (Blenheim Palace) to [Lady Randolph Churchill] thanking her for her letters and remarking on [a letter] from WSC. He also discusses: the future marriage of [Lord] Curzon [later 4th Lord Howe] to "Georgie" [Lady Georgiana Churchill, later Lady Curzon and Lady Howe] which he describes as "brilliant"; his poor health; and his opinion that it would be undesirable for her to have dinner with Mrs Beauclere alone; and arrangements for moving into a house.

Letter from Lord Randolph Churchill (29 St James' Place [London]) to [Lady Randolph Churchill] including: the annoyance of [Frances, Duchess of Marlborough] at [Lady Randolph] attending a ball; his approval of [his new footman] Frederick; a fight between [20th Lord] Shrewsbury [and Talbot] and [Alfred] Mundy; a planned visit to the zoological [society] by Elizabeth Everest, WSC and [John S Churchill]; and Lord Randolph's opinion that WSC is bored of his holiday.

Letter from Lord Randolph Churchill (Villa Carmen, Monte Carlo [Monaco]) to [Lady Randolph Churchill] including: his apologies for forgetting her birthday; arrangements for her journey to Monte Carlo; Annie's position [Duchess of Roxburghe, earlier Lady Anne Churchill and Lady Bowmont] as Mistress of the Robes; observations on the dullness of letters from [Sir Henry Drummond] Wolff; and a request that she should give WSC some money before he returns to school.

Letter from Lord Randolph Churchill (Government House, Bombay [India]) to [Lady Randolph Churchill] including: birthday greetings; comments on the "adventures" had by WSC; arguments between Leonie [Leslie, earlier Leonie Jerome] and the Leslie family; his opinion of Parsee practices; descriptions of his social engagements and those he has met, who included leading native politicians; his itinerary and a request that she should tell "Winnie" [WSC] that he has received his letter.

Letter from Lord Randolph Churchill (Residency Lucknow [India]) to [Lady Randolph Churchill] including: thanks for her letters and a request that she thank "little Winny" [WSC] for his letter which Lord Randolph describes as well written; his annoyance at a letter from [Sir Henry Drummond] Wolff; his poor opinion of the English in Lucknow; and observations on a meeting with the natives of Lucknow.

Letter from Lord Randolph Churchill (Auchnashellach [Dingwall, Ross and Cromarty, Scotland] on the notepaper of the India Office) to [Lady Randolph Churchill] including sympathy for the difficulties experienced by Clara [Frewen, earlier Clara Jerome] in childbirth; a message for [Henry] Chaplin; his success at fishing; and the hope that she has provided some entertainment for "Winny" [WSC].

Letter from Lord Randolph Churchill (Makerstoun House, Kelso [Roxburghshire]) to Jennie [Lady Randolph Churchill] including: the success of a racehorse called Renard; the people he has met; comments on the British government's policy on Uganda and a visit to Harrow to see WSC and John S Churchill at which [James] Welldon had discussed the likelihood that WSC would pass his next examination.

Letter from Lord Randolph Churchill (50 Grosvenor Square [London]) to [Lady Randolph Churchill] describing his journey and a hunting expedition with the Meath hounds and discussing his bedroom furniture. He adds that he has sent WSC a copy of his Sandhurst examination marks commenting that he should be pleased with his position of eighth despite criticism for impunctuality.

Letter from Lord Randolph Churchill (Le Nid [Monte Carlo, Monaco]) to [Lady Randolph Churchill] describing a trip to Nice [France] and the people he has met who include "Ronny" [Ronald] Greville and attempts by the Duchess of Montrose to "take the Nid by storm". He also discusses WSC's riding expenses and asks her to draw WSC's attention to "expressions of authority".