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 WSC (50 Grosvenor Square [London]) to "Mamma" [Lady Randolph Churchill] informing her that "Missy" [a pet] has recovered and that Captain [Walter] James [tutor at the crammer school to which WSC was sent] has predicted that he will pass [the Sandhurst entrance examination].

Letter from WSC (Grand Hotel, Splendide, Lugano [Switzerland]) to "Mamma" [Lady Randolph Churchill] describing Lugano and saying that he thinks that he is making progress with his French.

Letter from WSC (Continental Hotel, Milan [Italy]) to "Papa" [Lord Randolph Churchill] replying to his letter [see CHAR 1/2/66-68]. WSC says that he will try and alter his father's poor opinion of him through his work and conduct at Sandhurst and describes Milan.

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 "Jack" [John S Churchill] ([Brighton, East Sussex]) to "Papa" [Lord Randolph Churchill] asking him to send him autographs and photographs and reports that Miss Thomson considers that "Winny" [WSC] is "a very good boy" and that WSC is going to write a Greek play for Christmas.

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 (Banstead Manor, Newmarket [Suffolk]) to [Lady Randolph Churchill] reporting that [WSC and John S Churchill] have been good and that WSC rides well. He also relates his anger about arrangements for racing [his racehorse] Inverness and that WSC has made friends with the servants and is "full of local gossip".

Letter from Lord Randolph Churchill (Cliveden, Maidenhead [Buckinghamshire]) to [Lady Randolph Churchill] reporting his safe arrival at Cliveden; describing an evening spent at Moulton [Paddocks, Newmarket, Suffolk] where "Lady G" was amusing about her lovers and his success at the races at Windsor [Berkshire]; and commenting that [WSC and John S Churchill] are well and "permit us to lead a fairly tranquil existence".