Letter from Lord Randolph Churchill (Woodstock [Oxfordshire]) to [Lady Randolph Churchill] including: the pain caused by his rheumatism; dress material he has purchased for her; and his intention to bring WSC to England if he does not get stronger. He encloses a cheque for her to use to pay wages and discusses the necessity of securing a loan.

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 (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 (2 Connaught Place [London]) to [Lady Randolph Churchill] informing her that he intends to travel to Newmarket [Suffolk] that afternoon, advising her not to spend her money on a new brougham commenting "you seem rather like Winston [WSC] about money", and describing those he has met in London who include "Natty" [1st Lord Rothschild] and [Count Charles Kinsky].

Letter from Lord Randolph Churchill (Moulton Paddocks, Newmarket [Suffolk]) to [Lady Randolph Churchill] thanking her for her letter, describing his success at the races where he has "cleared a monkey [o500]", relating the friendliness of [Albert Edward] Prince of Wales returning a letter [not present] from WSC.

Letter from Lord Randolph Churchill (Royal Station Hotel, York) to [Lady Randolph Churchill] in which he tells her that he is down o300 through losses at the races; discusses the possibility that Sir [?] Jatton may buy his racehorse the Abbesse for o3,000 and enclosing a bill [not present] for WSC.

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 (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 (Banstead Manor, Newmarket [Suffolk]) to [Lady Randolph Churchill] discussing financial affairs and his pleasure with a bay pony he has purchased, reporting that [Frances, Duchess of Marlborough, WSC and John S Churchill] are leaving to go to Cliefden [Cliveden, Buckinghamshire] where he will join them and enclosing newspaper cuttings [not present].

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 (Le Grand Hotel, Monte Carlo [Monaco]) to [Lady Randolph Churchill] in which he describes the leisurely way he spends his days and a visit to Nice [France]; speculates on the likelihood of a dissolution of Parliament and asks her to wish WSC a happy birthday on his behalf.

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".