Illustrated card from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Papa" [Lord Randolph Churchill] in which he reproaches his father for not visiting him when he was in Brighton, describes visiting a museum and asks his father to send more copies of his autograph.

Letter from "Winny" [WSC] (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mama" [Lady Randolph Churchill] thanking her for her "epistle" and reporting that he has seen [Frances, Duchess of Marlborough].

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to "Mamma" [Lady Randolph Churchill] informing her of his safe arrival, asking her not to let his bad behaviour influence his summer holidays and reporting that he has made good progress with Euclid.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lord Randolph Churchill] in which he expresses his pleasure that he is going to Harrow [School] rather than Winchester [School]; discusses his progress with Euclid, arithmetic and Greek; reports that he is to play roles in plays by Moliere and Aristophanes and says that he wished that his father could attend the distribution of prizes.

Letter from WSC (29 & 30 Brunswick Road, Brighton [Hove, East Sussex]) to [Lady Randolph Churchill] in which he says that he would like her and [Lord Randolph Churchill] to attend the distribution of prizes, discusses his birthday party and the future examinations, and asks for more of her autographs as "there is rather a demand for them here".

Note from Elizabeth Layton [Secretary to WSC] to WSC informing him that Lord Blandford [later John, 11th Duke of Marlborough] will be at home for a week's leave from Saturday 30 Jun. [Typescript] With tick in red ink by ? WSC.

Note from Jo Sturdee [later Lady Onslow, personal secretary to WSC] to John Colville [Prime Minister's Private Secretary] stating that CSC has kept the photographs for her scrap book and thinks that a message of thanks should be sent from WSC to General Sir Frederick Pile [General Officer Commanding in Chief Anti-Aircraft Command]. [Typescript].

Letter from WSC to General Sir Frederick Pile [General Officer Commanding in Chief Anti-Aircraft Command] thanking him for the photographs of Mary [Mary Churchill, later Lady Soames] taken with her Battery in Belgium and on the cross-Channel journey, and stating that CSC is keeping them for her scrapbook. [Carbon].

Press cutting entitled "The Great Sarah" reporting remarks made by CSC referring to those qualities of Sarah, 1st Duchess of Marlborough which she would try to avoid [sent to WSC by Lord Beaverbrook].

WSC's history notebook, [from ?Harrow School] containing notes on: The War of the Spanish Succession, with accounts and maps of the First Duke of Marlborough's campaigns, The Literature of Queen Anne's Reign, The Darien Scheme, Scotch Affairs, 1702-1714, The Fortunes of Parties, 1702-1714, The Reign of George I, The Reign of George II.

Photograph of interior of [? Bladon Church, Woodstock, Oxfordshire].

Hymn card for Lord Randolph Churchill's burial service, Bladon, Oxfordshire.

Letter from Lady Randolph Churchill, Banstead, to WSC, on his toothache, advising him to brush his teeth more frequently, also on the Newmarket races.

Letter from Lady Randolph Churchill, Banstead, to WSC, on his toothache, the Duchess of Marlborough's illness and the Newmarket races.

Letter from Lady Randolph Churchill, Oakley Court, Windsor, to WSC, apologies for not visiting him at Harrow, and hoping to see him the following week.

Letter from Lady Randolph Churchill to WSC, on his financial situation.

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, Banstead, to WSC, sending £1 and complaining about the state of his finances, also on his toothache, complaining that he had had another tooth out ".

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 Lady Randolph Churchill, 50 Grosvenor Square, London, to WSC, asking him to write, and criticising his new hat.

Letter from Lady Randolph Churchill, Sunningdale, to WSC, on her visit to the Ascot races, and on the Sandhurst entrance examination.