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 (Blenheim Palace) to "Jeannette" [Jennie Jerome, later Lady Randolph Churchill] including: his future journey to Paris [France] to see her; his joy at her father's [Leonard Jerome's] consent to their marriage; his duties as a magistrate at Woodstock [Oxfordshire]; Albert Edward, Prince of Wales' interest in them and Randolph's future visit to Paris.

Letter from Lord Randolph Churchill (Bedford Hotel, Brighton [East Sussex]) to [Lady Randolph Churchill] expressing his distress that WSC's fever has returned, enclosing a telegram [not present] and including directions for [Dr Robson] Roose as to where he is staying.

Letter from Lord Randolph Churchill (Welbeck Abbey, Worksop [Nottinghamshire]) to [Lady Randolph Churchill] including the names of those present at the party and those he met at the races on the previous day and reports concerning [Lord] Blandford [later George, 8th Duke of Marlborough].

Letter from Lord Randolph Churchill (2 Connaught Place [London]) to [Lady Randolph Churchill] including the end of excitement in the French Chamber at the election of the new president; a meeting about the unemployed in [South] Paddington [London] which resulted in the establishment of a relief fund; his intention to see WSC when he visits Brighton [East Sussex] and an outline of his planned itinerary.

Letter from Lord Randolph Churchill (Tarbes [France]) to [Lady Randolph Churchill] including: his impressions of Tarbes, [the Marquis de] Breteuil's unease at the possible effect of the arrival of Jeanne Granier, a French actress, on the local electorate; his desire that WSC should read during his school holidays and his outrage at the marriage of the Duke of Montrose.

Letter from Lord Randolph Churchill (Tarbes [France]) to [Lady Randolph Churchill] including his impressions of the area, his hope that she may be able to see [Marquis de] Breteuil in Egham [Surrey] at the end of August and a request that she should send his love to [WSC and John S Churchill].

Letter from Lord Randolph Churchill (Le Grand Hotel, Monte Carlo [Monaco]) to [Lady Randolph Churchill] in which he describes the company of "Johnny" Willoughby and [Archibald] Merry, his gambling record and the politicians who are present and who include [Aretas] Akers-Douglas [later Lord Chilston] and Henry Bonsor, and makes observations about the affairs of [Lady] Sarah [Churchill, later Sarah Wilson] whom he describes as a fool.

Letter from Lord Randolph Churchill (Moulton Paddocks, Newmarket [Suffolk]) to [Lady Randolph Churchill] describing a meeting with [Frances, Duchess of Marlborough] and Henry Fowler and his success at fishing. He says that he hopes to see her in London the following week, speculates on the success of various racehorses, and comments on a "capital letter" sent to him by WSC.

Letter from Lord Randolph Churchill (2 Connaught Place [London]) to [Lady Randolph Churchill] informing her that he is going to Blenheim at the request of [George, 8th Duke of Marlborough], commenting on a discussion he has had about Birmingham political matters and speculating about broader political issues.

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".

Letter from Lord Randolph Churchill (Cliveden, Maidenhead [Buckinghamshire]) to [Lady Randolph Churchill] discussing financial matters and asking her to be more careful; describing an expedition to Oxford with [Lady] Sarah [Churchill, later Sarah Wilson], WSC and "Jack" [John S Churchill] and "Jack's" first ride on his pony and discussing arrangements for her to come to Cliveden.

Letter from Lord Randolph Churchill (Hotel Bristol, Rome [Italy]) to [Lady Randolph Churchill] in which he expresses his admiration for [Charles] Parnell's manifesto and speculates on the future of the Home Rule alliance and the likelihood of a dissolution of parliament. He describes an evening spent with [1st Lord] Dufferin [and Ava] and says that he has received a letter from WSC "giving a glowing account of himself".

Letter from Lord Randolph Churchill (Minich, "On the Nile" [Egypt]) to [Lady Randolph Churchill] describing his travels on the Nile and the boat he is travelling in. He asks her to thank Moreton [Frewen] for his telegram regarding the [gold crushing] "machine" and to wish [WSC and John S Churchill] a happy Christmas and asks about the results of WSC's examination.

Letter from Lord Randolph Churchill (Johannesburg [South Africa]) to [Lady Randolph Churchill] including: descriptions of his activities at game hunting, letters to the Daily Graphic, travel plans and details of his investments; his relief at not being involved with the Tories; and his pleasure at a "capital letter" he has received from 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 WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] in which he says that he is looking forward to seeing her and [Lord Randolph Churchill], discusses the Harrow School entrance examination and his progress at school and requests dictionaries.

Letter from WSC ([Harrow School, Middlesex]) to [Lady Randolph Churchill] detailing his reports for the previous week, expressing his hopes for future good reports and asking her not to be cross with him saying "I am not lazy & untidy but careless & forgetful". Envelope present.