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
He was a descendant of John Churchill, 1st Duke of Marlborough, whose home it was.
Q 02Churchill's mother Jennie was the daughter of an American businessman named what?
Leonard Jerome
His mixed English and American parentage made him proud of both nations.
Q 03Whom did Churchill mourn as 'my dearest and most intimate friend' when she died in 1895?
His nanny, Elizabeth Everest
His parents were effectively estranged and his nanny had largely raised him and his brother.
Q 04Which military college did Churchill attend as a cavalry cadet before joining the army?
Sandhurst
He got in only on his third attempt, in September 1893.
Q 05What did Churchill call the recurring depression that dogged him through life?
His black dog
He treated it, Roy Jenkins says, largely by writing.
Q 06At which 1898 battle in Sudan did Churchill take part in one of the British Army's last cavalry charges?
Omdurman
He rode with the 21st Lancers and wrote a book about the campaign, The River War.
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 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
Her unbroken affection, biographers say, gave his turbulent career a secure background.
Q 11As President of the Board of Trade, Churchill's 1909 Labour Exchanges Bill aimed to help whom?
The unemployed find work
He also introduced trade boards establishing the principle of a minimum wage.
Q 12During which 1911 East End incident did Churchill controversially stand with police as a house burned?
The Siege of Sidney Street
He told the fire brigade not to enter, saying he would rather the house burn than risk British lives on ferocious rascals.
Q 13Which new word did Churchill coin as First Lord of the Admiralty?
Seaplane
Q 21What did Churchill call his time out of office in the 1930s, when he warned about Nazi Germany?
His wilderness years
Civil servants secretly fed him data on German rearmament.
Q 22How did Churchill describe the 1938 Munich Agreement in the Commons?
"A total and unmitigated defeat"
He had urged Chamberlain to threaten war if Germany invaded Czechoslovakia.
Q 23Which German ship did HMS Cossack board in Norwegian waters in 1940, freeing 299 seamen?
The Altmark
The action enhanced his reputation during the Phoney War.
He ordered 100 of them built and pushed the fledgling Royal Naval Air Service.
Q 14Churchill was blamed for which failed 1915 campaign, which cost him the Admiralty?
Gallipoli
The Conservatives made his removal a condition of joining Asquith's coalition.
Q 15After resigning in 1915, Churchill commanded which battalion on the Western Front?
The 6th Royal Scots Fusiliers
He served about six months near Ploegsteert before returning to Parliament.
Q 16Churchill bought which Kent country house in 1922, doing much of its brickwork himself?
Chartwell
He built garden walls there himself as an amateur bricklayer.
Q 17After 1922, Churchill wrote that he was without an office, without a party, and without what else?
An appendix
He rejoined the Conservatives and was Chancellor of the Exchequer within two years.
Q 18As Chancellor in 1925, Churchill controversially restored Britain to what, against Keynes's advice?
The gold standard
The return, at the 1914 parity, is held to have caused deflation and hurt the coal industry.
Q 19During the 1926 General Strike, which government propaganda paper did Churchill edit?
British Gazette
After the strike he acted as an intermediary between the miners and their employers.
Q 20Churchill called which Indian leader 'a seditious Middle Temple lawyer, now posing as a fakir'?
Gandhi
He resigned from the Shadow Cabinet in 1931 over Dominion status for India.
Q 24Whom did Churchill succeed as prime minister in May 1940?
Neville Chamberlain
His only rival, Lord Halifax, admitted he could not govern effectively from the House of Lords.
Q 25Which new post did Churchill create and assume, making him the most powerful wartime PM in history?
Minister of Defence
He brought outside experts like Beaverbrook and Lindemann into government.
Q 26What did Churchill offer 'but blood, toil, tears and sweat' in his first speech as prime minister?
His policy was to wage war and his aim was victory
He turned a childhood lisp into an asset, mocking Hitler as a Nar-zee.
Q 27How many Allied servicemen were evacuated from Dunkirk in Operation Dynamo?
About 338,000
Churchill called it a miracle of deliverance but warned 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
It was a clear appeal to the still-neutral United States.
Q 29Churchill's 18 June 1940 speech, saying men would call this the noblest of times, is known as what?
Their finest hour
He expected the Battle of Britain to begin.
Q 30What did Churchill tell Hugh Dalton to do with the newly formed Special Operations Executive?
"Set Europe ablaze"
The SOE was to promote subversion in Nazi-occupied Europe.