Letter from "Jack" [John S Churchill] (Standerton [South Africa]) to "Mama" [Lady Randolph Churchill] in which he says that despite skirmishes with the Boers and the Free Staters the regiment is "very bored and tired", reports that Olive Guthrie saw some fighting at Blomfontein, and comments on WSC's escape.

Letter from Lord Randolph Churchill (Pretoria [South Africa]) to [Lady Randolph Churchill] in which he describes his journey, anticipates that his letters to the Daily Graphic will anger the Boers, and praises Gwynydd [Williams] as a secretary and discusses [Lady Randolph's] activities in London.

Letter from Lord Randolph Churchill (Pietersberg [South Africa]) to [Lady Randolph Churchill] in which he describes his journey and the amusement provided by cooking his own food, and relates a comment which he made to Gwynydd [Williams his secretary] that business was progressing so well that he felt like Polycrates.

Letter from Lord Randolph Churchill ("In Camp", Fort Tuli [Rhodesia]) to [Lady Randolph Churchill] in which he describes his journey and living conditions, comments on the success of the expedition, outlines his plans for game hunting, and speculates on the effect of his letters to the Daily Graphic.

Letter from WSC (Chieveley Camp, Natal [South Africa]) to "Mamma" [Lady Randolph Churchill] in which he discusses "Jack's" [John S Churchill] conduct in the fighting and asks her not to allow him to leave [the hospital ship] Maine before fully recovered and to send him reviews of his book ["The River War"]. He informs her that he has been invited to become President of the Midland Conservative Club and says that he would like to receive more brandy.

Letter from WSC (Monte Cristo Mountain, near Chieveley, Natal [South Africa]) to "Mamma" [Lady Randolph Churchill] in which he describes manoeuvres against the Boer forces which he hopes will relieve Ladysmith. He encloses a telegram [not present] and discusses the action which should be taken about it. Envelope present.

Part of a letter from WSC [to Lady Randolph Churchill] in which he discusses the possibility that she might be able to "plaster" over an injury [to Count de Bendern] and his correspondence with King [Edward VII] about South Africa and WSC's stay with [Kaiser Wilhelm II].

Letter from WSC (Madeira "en route") to "Mamma" [Lady Randolph Churchill] in which he says that the sea has been very rough and that Sir Redvers Buller is "well disposed" towards him and speculates on the progress [of the Boer War].

Letter from WSC (RMS Dunotta Castle "en route") to "Mamma" [Lady Randolph Churchill] speculating on the progress of the [Boer War] and on the publication of ["The River War"] and asking her to send copies to Pamela [Plowden, later Lady Lytton] and to [Charles, 9th Duke of] Marlborough. Manuscript in the hand of WSC.

Letter from WSC ("In the train near East London", South Africa]) to "Mamma" [Lady Randolph Churchill] informing her that he is travelling to Natal with Captain [Alexander] Campbell and [John] Atkins from the Manchester Guardian. He observes that the Boer forces have been underestimated and that there will be "a fierce and bloody struggle" and expresses his hope that he is ahead of other newspaper correspondents.

Letter from "Jack" [John S Churchill] (Field Hospital, Charleston [South Africa]) to "Mama" [Lady Randolph Churchill] in which he says that he has been injured while playing polo; describes his journey in a Swiss red cross ambulance; and says that he would like to return home although he will wait until the regiment is disbanded as that would be "the right thing to do".

Letter from "Jack" [John S Churchill] (Beyond Lydenburg [South Africa]) to WSC including: his injury while playing polo; meetings with [1st] Lord Roberts and with a civilian who had helped WSC escape; the death of [Albert] Savory; his opinion of [Redvers] Buller; fighting and losses sustained by the "R[ifle] B[rigade]'s"; a horseback charge against the Boers in which he participated; his hopes to return home and the high opinion of WSC among the headquarters staff.

Letter from "Jack" [John S Churchill] (Lydenburg [South Africa]) to WSC including: his regiment's action and losses sustained; the intention to keep the Boers in the "fever district"; lack of provisions; his intention to return home; dissatisfaction between the Natal army and the "other side". In a postscript he asks him to write to Isabel Savory concerning the death of [Albert] Savory. Two typed transcriptions of the letter at end of file.

Letter from "Jack" [John S Churchill] (Helvetia, Second Cavalry Brigade [South Africa]) to "Mama" [Lady Randolph Churchill] including: [1st] Lord Roberts' kindness towards him; a meeting with a man who helped WSC escape; the fighting which he had witnessed; the terrible sight of the wounded and the dead and his hopes that the war is almost at an end. Four typed copies of the letter at end of file.

Letter from "Jack" [John S Churchill] (Lydenburg [South Africa]) to "Mama" [Lady Randolph Churchill] including: the lack of opposition by the Boers to a march which his regiment conducted; an attack on the camp by Boer forces; the imminent disbanding of the regiment; his hopes to come home and relief that he remained "to the end" and his poor physical condition. Two typed copies of the letter at end of file.

Letter from WSC (Bloemfontein [South Africa]) to "Jack" [John S Churchill] in which he discusses an imminent attack on Brandfort and speculates on the [Boer] War, gives news of [Charles, 9th Duke of] Marlborough, Ivor Guest [later Lord Ashby St Ledgers and 2nd Lord Wimborne] and Victor [2nd Lord Lytton], and recommends that Jack reads his accounts in the Morning Post. Signed typescript. Typed transcript at CHAR 28/152B/182-185.

Transcript of a letter from WSC (Bloemfontein [South Africa]) to "Jack" [John S Churchill] in which he discusses an imminent attack on Brandfort and speculates on the [Boer] War, gives news of [Charles, 9th Duke of] Marlborough, Ivor Guest [later Lord Ashby St Ledgers and 2nd Lord Wimborne] and Victor [2nd Lord Lytton], and recommends that Jack reads his accounts in the Morning Post. Typed. 2 copies. Original letter at CHAR 28/152B/181.

Letter from WSC (Pretoria [South Africa]) to "Jack" [John S Churchill] including: the news that he plans to go home "after an interesting and exciting march" with General [Sir Ian] Hamilton; news of Hugo [Baring] and of the death of the son of [3rd Lord] Chesham; advice to leave the South African Light Horse and "come home to the quills of the city and the arms of the ladies". Signed typescript.

Letter from Lord Randolph Churchill (Hartley Hill [Rhodesia, later Zimbabwe]) to [Lady Randolph Churchill] in which he sympathises with the failure of the Paddington Polytechnic, expresses his disappointment in the gold fields; describes his success at game hunting and his daily life.