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 (Novar, Evanton, Ross-shire [Ross and Cromarty, Scotland]) to [Lady Randolph Churchill] thanking her for her letters to him and requesting that she should thank WSC for his letter, approving of her decision to send "Jack" [John S Churchill] to Brighton [East Sussex] and predicting that [Sir] Charles Legard's letter [to the newspapers] will not harm him.

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 (2 Connaught Place [London]) to [Lady Randolph Churchill] thanking her for her letter and discussing his future visit to Paris [France] with [Henry] Chaplin and "Tommy" [WH] Trafford. He also reports on WSC's health and enjoyment of a locomotive steam train; a successful speech he has made in Parliament which had pleased the Whigs; and comments about "GOM" [Grand Old Man, William Gladstone] "He is the wickedest old devil any country ever produced".

Drawing of WSC as a small child on a red sofa. Includes frame.

Letter from [Lady Randolph Churchill] (Belfast [Ulster, Ireland]) to "R" [Lord Randolph Churchill] in which she says that she has visited church twice and that she has been looking after the baby [WSC], that she hopes that [Lord] Blandford [later George, 8th Duke of Marlborough] will not mind him returning to her soon.

Letter from [Lady Randolph Churchill] to [Lord Randolph Churchill] in which she discusses the pain of being separated from him, breakfast with [Henry] Standish and [Helene] Standish, reports compliments on her skating from Madame de Sagan and says that she is not lonely with "dear Winston"[WSC].

Letter from [Lady Randolph Churchill]([Dublin, Ireland]) to [Lord Randolph Churchill] in which she describes the visitors she has received who include the Duke of Abercorn and [John, 7th Duke of Marlborough]; riding; invitations; the noise made by WSC and the running of the house with only one servant named Kate. Includes a cross marked "W [WSC] signature.

Letter from [Lady Randolph Churchill](Vice Regal Lodge, Dublin [Ireland]) to "R" [Lord Randolph Churchill] in which she says that she is bored, comments on a vulgar letter to [Lady] Rosamund [Churchill, later Lady Fellowes and Lady De Ramsey] and the date of Rosamund's wedding, and gives news of WSC.

Letter from [Lady Randolph Churchill] to "R" [Lord Randolph Churchill] in which she describes a morning with Mrs [Emelina] Guinness; reports on the purchase of a toy elephant for WSC; thanks him for buying her a saddle and complains of a cold.

Letter from [Lady Randolph Churchill] to "R" [Lord Randolph Churchill] in which she discusses riding and the progress of a horse, clothes for Thomas and a walk with WSC.

Part of a letter from [Lady Randolph Churchill] to [Lord Randolph Churchill] including: her loneliness; a conversation with "Annie" [Lady Bowmont, later Duchess of Roxburghe, earlier Lady Anne Churchill] who had said that she was "very much bored" at being pregnant; a visit to Dublin [Ireland] and a message from WSC.

Part of a letter from [Lady Randolph Churchill] to [Lord Randolph Churchill] including: the announcement of the engagement of [Lady Rosamund Churchill, later Lady Fellowes and Lady De Ramsey to William Fellowes, later 2nd Lord De Ramsey]; a report in the Morning Post about his "remarks"; Lady Castlereagh's [later Lady Londonderry's] comments on the arguments between her family and the Marlboroughs; and WSC's progress.

Part of a letter from [Lady Randolph Churchill] to [Lord Randolph Churchill] in which she says that she will inform people that [5th Lord] Rossmore [formerly Derrick Westenra] had called on her so that it would not appear that she was trying to hide it and reports that WSC is teething.

Part of a letter from [Lady Randolph Churchill] to [Lord Randolph Churchill] in which she asks whether she has met any of their "enemies" [a reference to Lord Randolph's quarrel with Albert Edward, Prince of Wales]; reports that [Lord] Blandford [later George, 8th Duke of Marlborough] is at Berne [Germany]; comments that she thinks that [Elizabeth] Everest is cross with her for taking WSC out and discusses Colonel Frazer.

Letter from [Lady Randolph Churchill] to [Lord Randolph Churchill] in which she describes a trip to the circus with WSC; promises to work on her painting, requests that he should enquire about her fans and says that she may stay with "Annie" [Lady Bowmont, later Duchess of Roxburghe, earlier Lady Anne Churchill] for the wedding of [Lady] Rosamund [Churchill, later Lady Fellowes and Lady De Ramsey].

Letter from [Lady Randolph Churchill] to [Lord Randolph Churchill] in which she describes a church service in the Chapel Royal; comments on [Lord] Clanmorris withdrawing an invitation to his yacht as [the Duke of] Connaught [and Strathearn] wished to sail; reports that WSC spent the day with the son of Mrs [Emelina] Guinness and describes the rings which [William] Fellowes [later 2nd Lord De Ramsey] has given to [Lady] Rosamund Churchill[ later Lady Fellowes and Lady de Ramsey].

Letter from [Lady Randolph Churchill] to [Lord Randolph Churchill] including: comments about a visit to Carton [Maynooth, County Kildare, Ireland]; the jealousy of [Lady] Rosamund [Churchill, later Lady Fellowes and Lady De Ramsey] at [Lady Randolph's] ring; observations that WSC is well and "chatters 19 to the dozen as usual"; her boredom [in Dublin, Ireland]; progress at painting; irritation with Kildare and acknowledgement of the receipt of a cheque.

Letter from [Lady Randolph Churchill] to [Lord Randolph Churchill] in which she reports that [Frances, Duchess of Marlborough] has read out Lady Londonderry's comments about him, says that she has avoided seeing [the Duke of] Connaught [and Strathearn] and that WSC has been behaving ridiculously by saying to Cottlehurst "Goodbye little chap".