Winston Churchill Trivia
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70 free Winston Churchill trivia questions with answers — history quiz, new questions added Aug 2026.
This Winston Churchill trivia quiz covers the whole of his long life: the aristocrat born at Blenheim, the war correspondent who escaped a Boer prison camp, the MP who crossed the floor twice, the First Lord blamed for Gallipoli, the Chancellor who returned Britain to the gold standard, the lone voice of the wilderness years, the prime minister of 1940 and the great speeches, the loser of 1945, the Iron Curtain orator, and the Nobel laureate given a state funeral in 1965. The easy questions cover the outline: his birthplace, his two wartime terms, his most famous speeches, the war he led Britain through and his literary prize. The harder half is for readers of Roy Jenkins and Andrew Roberts: the nanny he mourned, the depression he called his black dog, the word 'seaplane' he coined, the two parties he defected between, the Sidney Street siege, the six months in the trenches, the appendix line of 1922, the fakir jibe at Gandhi, the Altmark boarding, the 'set Europe ablaze' order, the naval battle that turned the tide of the U-boat war, the pseudonym he painted under, the honorary US citizenship, and the portrait Clementine had destroyed. Every answer was checked against Winston Churchill's encyclopaedia entry before publishing. If you enjoy this, try our World War II, British prime ministers and Franklin Roosevelt quizzes next.
30 of 70 questions with answers and explanations. Play the quiz
Q 01At which grand house was Churchill born in November 1874?
Blenheim Palace
Blenheim Palace was Queen Anne's and Parliament's reward to his ancestor John Churchill, 1st Duke of Marlborough, for his 1704 triumph at Blenheim.
Q 02Churchill's mother Jennie was the daughter of an American businessman named what?
Leonard Jerome
Leonard Jerome, a stock speculator dubbed the King of Wall Street, helped build Jerome Park Racetrack, where the first Belmont Stakes was run in 1867.
Q 03Whom did Churchill mourn as 'my dearest and most intimate friend' when she died in 1895?
His nanny, Elizabeth Everest
His nanny Elizabeth Everest, whom he called Woom, had cared for him since infancy; he attended her funeral and paid for her headstone.
Q 04Which military college did Churchill attend as a cavalry cadet before joining the army?
Sandhurst
Sandhurst admitted him in September 1893, but only after he had failed its entrance exam twice.
Q 05What did Churchill call the recurring depression that troubled him through life?
His black dog
Churchill named his recurring depression his black dog, and biographer Roy Jenkins saw writing as his chief defence against it.
Q 06At which 1898 battle in Sudan did Churchill take part in one of the British Army's last cavalry charges?
Omdurman
Omdurman saw him charge as a 21st Lancers subaltern, though he was a 4th Hussars officer on attachment; he later wrote The River War about the campaign.
Q 07During the Second Boer War, Churchill was captured after Boer shelling derailed what?
His armoured train
He was interned in Pretoria; his dramatic escape weeks later made him famous.
Q 08How did Churchill escape his Boer captors in December 1899?
By stowing away on freight trains and hiding in a mine
He made it to Portuguese East Africa, and the escape brought him great publicity.
Q 09In 1904 Churchill 'crossed the floor' from the Conservatives to which party?
The Liberals
He joined the Liberals as a free trader in 1904, then crossed back to the Conservatives twenty years later, in 1924.
Q 10Whom did Churchill marry in September 1908 at St Margaret's, Westminster?
Clementine Hozier
Clementine Hozier accepted his proposal that August, and their marriage lasted more than 56 years, until his death in January 1965.
Q 11As President of the Board of Trade, what did Churchill's 1909 Trade Boards Act let boards set?
Minimum wages
Minimum wages set by the new boards were legally enforceable, so exploitative employers could be prosecuted.
Q 12During which 1911 East End incident did Churchill controversially stand with police as a house burned?
The Siege of Sidney Street
The Siege of Sidney Street, where members of a Latvian gang who had killed three policemen were holed up in a Stepney house.
Q 13Which word is Churchill said to have coined as First Lord of the Admiralty?
Seaplane
Seaplane, a coinage credited to Churchill; the word dates from 1913, while he was running the Admiralty.
Q 21What name is given to Churchill's 1930s spell out of office, when he warned about Nazi Germany?
His wilderness years
His wilderness years, when officials Desmond Morton and Ralph Wigram secretly fed him figures on German rearmament.
Q 22How did Churchill describe the 1938 Munich Agreement in the Commons?
"A total and unmitigated defeat"
"A total and unmitigated defeat", he told MPs on 5 October 1938, adding that France had suffered even more than Britain.
Q 23On Churchill's orders in 1940, HMS Cossack boarded which German ship in Norwegian waters, freeing 299 seamen?
The Altmark
Q 14Churchill was blamed for which failed 1915 campaign, which cost him the Admiralty?
Gallipoli
Gallipoli: the Conservatives, who detested him as a defector, made his removal from the Admiralty their condition for joining Asquith's coalition.
Q 15As First Lord of the Admiralty, Churchill backed which new weapon, first used at the Somme in September 1916?
The tank
The tank: to keep the machines secret, they were passed off as water carriers, and 'tank' began as a code name.
Q 16Which Kent country house did Churchill buy in 1922?
Chartwell
Chartwell, near Westerham, which remained the Churchills' family home until his death in 1965.
Q 17Churchill joked that after the 1922 election he was without an office, a seat, a party and what?
An appendix
An appendix: surgeons removed it in October 1922, and the weakness that followed left him barely able to campaign in Dundee.
Q 18As Chancellor in 1925, Churchill controversially restored Britain to what, against Keynes's advice?
The gold standard
The gold standard, at its pre-war rate; critics blame the decision for depressing the economy and raising unemployment.
Q 19During the 1926 General Strike, which government propaganda paper did Churchill edit?
British Gazette
The British Gazette: Churchill even requisitioned newsprint, forcing the strikers' British Worker down from eight pages to four.
Q 20Which Indian leader did Churchill scorn in 1931 as a seditious lawyer turned fakir?
Gandhi
Gandhi, who had himself trained as a barrister at London's Inner Temple.
The Altmark, supply ship to the Admiral Graf Spee, was carrying seamen captured from ships the raider had sunk.
Q 24Whom did Churchill succeed as prime minister in May 1940?
Neville Chamberlain
Neville Chamberlain, days after Leo Amery told him in the Commons, quoting Cromwell, 'In the name of God, go!'
Q 25Which new post did Churchill create and take, making him Britain's most powerful wartime prime minister?
Minister of Defence
Minister of Defence; he also brought in outside experts, such as the physicist Frederick Lindemann as his scientific adviser.
Q 26Which one word did Churchill give as Britain's aim in his 'blood, toil, tears and sweat' speech?
Victory
Victory: 'victory at all costs, victory in spite of all terror', because without victory there is no survival.
Q 27Churchill hailed 'a miracle of deliverance' after which 1940 operation rescued about 338,000 Allied troops?
Dynamo
Dynamo: yet Churchill warned MPs that 'wars are not won by evacuations.'
Q 28In which speech did Churchill vow to fight on the beaches and never surrender?
His Dunkirk address of 4 June 1940
His Dunkirk address of 4 June 1940 closes by looking to the New World to step forth to the rescue, a clear appeal to the neutral United States.
Q 29Churchill's 18 June 1940 speech, declaring the Battle of France over, is known as what?
Their finest hour
Their finest hour: he told MPs he expected the Battle of Britain was about to begin.
Q 30What did Churchill tell Hugh Dalton to do with the newly formed Special Operations Executive?
"Set Europe ablaze"
'Set Europe ablaze': he said it on 22 July 1940, the day the SOE was formed to run sabotage and resistance in occupied Europe.