Letter from Charlotte Thomson to WSC, on Brunswick Road School, Brighton.

Letter from Louis Moriarty, Army Class Master, Harrow School, to WSC, on WSC's "very creditable" failure in the Sandhurst entrance examination. Stating that if he worked "earnestly and sensibly" he would pass in November.

Letter from Rev. James Welldon, Headmaster, Harrow School, to WSC, on his failure in the Sandhurst entrance examination. Urging him to work "not by fits and starts but with regular persistent industry". Commenting that the grammatical foundation of his language was so uncertain that he lost marks which other boys gained "You therefore have ground to make up as well as new ground to cover".

Letter from Lady Randolph Churchill, 2 Connaught Place, London, to WSC, congratulations on obtaining Remove [into the First Division of the Fourth Form at Harrow], hoping that he would continue to work. Asking him to write at least twice a week.

Letter from Lady Randolph Churchill, 2 Connaught Place, London, to WSC, on his "very bad" school report from Harrow Describing his work as an "insult to his intelligence", and contrasting him to his brother Jack "who comes out at the head of his class every week".

Letter from Lady Randolph Churchill, Banstead, to WSC, apologies for not visiting him at Harrow, and advising him not to sell his bicycle and buy a bulldog puppy "a dog is sometimes a nuisance".

Letter from Lady Randolph Churchill, Iwerne Minster House, Blandford, to WSC, on his school report "You must try & have a better one next term as Papa will be back & will expect glowing accounts of yr work." Also commenting on a day's hunting, and "cutting a lovely somersault" at the 3rd fence.

Letter from Maggie Gooderidge, former servant of WSC's family, "better known as Maggie from Blenheim" (Chadderton Street, London W1) to WSC, with sympathy on his road accident in New York [United States] and a reminiscence about his childhood.

Letter from Louis Moriarty (Hillside, Harrow, [Middlesex]) to WSC congratulating him on his appointment as Under- Secretary of State for the Colonies and recalling his time as WSC's tutor.

Letter from Lord Randolph Churchill ([Rutland Cottage] Newmarket [Suffolk]) to [Lady Randolph Churchill] thanking her for her letters, describing the races at Newmarket, discussing the sale of a house and instructing her to take care of the baby [WSC].

Letter from Lord Randolph Churchill ([Rutland Cottage] Newmarket [Suffolk]) to [Lady Randolph Churchill] describing his success at the races and expressing his pleasure that the baby [WSC] is better.

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 (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 (Fort Salisbury [Rhodesia, later Harare, Zimbabwe]) to [Lady Randolph Churchill] in which he explains that he is waiting for [Cecil] Rhodes as he would like to discuss South African issues with him, speculates on British political affairs, and enquires about WSC's French lessons.

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 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.