Multiple Choice Trivia Quiz Questions about Winston Churchill

When Churchill died, President Eisenhower paid him a very warm tribute. With reference to the Americans and British that had endured World War 2 Eisenhower said of Churchill:

“To those men Winston Churchill was Britain—he was the embodiment of British defiance to threat, her courage in adversity, her calmness in danger, her moderation in success. Among the Allies his name was spoken with respect, and admiration and affection. Although they loved to chuckle at his foibles, they knew he was a staunch friend. They felt his inspirational leadership. They counted him a fighter in their ranks“.

That short extract from Eisenhower’s eulogy provides us with an excellent snapshot of Churchill’s legacy. Over time he has become a very controversial figure; a situation that any Brit celebrating on VE Day in 1945 could never have imagined. In May 1945 Churchill’s opinion poll approval rating was at a whopping 83% which is a perfect reflection of how the general population felt about him at that time and the enormity of their gratitude for his contribution to ending the war and also ensuring that the United Kingdom was so well defended between 1939 and 1945.



Even though his political party (the Conservatives) lost their seat in Parliament in the July 1945 general election the reputation that he had earned throughout the Second World War meant that he had respect the world over and many important people still wanted to hear his opinions and views. So, even though he had to step down as Prime Minister and become Leader of the Opposition he continued to have significant influence on world politics and policy.

The International Churchill Society (ICS) was formed soon after Churchill’s death and their mission is to preserve his significant legacy and educate the world about his life and achievements.

Here are our online multiple choice Winston Churchill trivia quiz questions …

Good luck ...

Question 1. Where was Winston Churchill born in 1874?
Question 2. At what age did he begin boarding school at St. George's School in Ascot?
Question 3. Churchill's father (Lord Randolph Churchill) wanted him to have a military career so Churchill spent his last three years at Harrow preparing to join a military academy. On which attempt did Churchill finally gain entrance to Sandhurst Royal Military Academy?
Question 4. At what age did Winston Churchill write his first book 'The Story of the Malakand Field Force' ?
Question 5. Which political party did Winston Churchill represent when he first took his seat in the House of Commons in February 1901?
Question 6. Following the outbreak of World War One in 2014, Churchill was initially responsible for the warfare effort of the ...?
Question 7. Britain declared war on Germany on 3rd September 1939 but when did Churchill subsequently become Prime Minister of Great Britain?
Question 8. Churchill was famous for his wartime speeches. His very first speech in the Houses of Parliament included the following famous line: "I would say to the House, as I said to those who have joined this government, that I have nothing to offer but ...?"
Question 9. During World War 2 many officials wanted to move the seat of government away from London for safety. Churchill disagreed and instead made regular use of underground Cabinet War Rooms beneath which important building?
Question 10. In January 1943, Churchill met with Roosevelt and General Charles de Gaulle where they agreed (in the 'Casablanca Declaration') that the Allies would accept nothing less than unconditional surrender from the Axis powers. Soon after he became seriously ill and had to rest for over a month. What illness did he have?
Question 11. D-Day (properly known as Operation Neptune) kick-started the  liberation of German-occupied France. Winston Churchill hoped to be part of the  Normandy invasion and planned to sail across the Channel on D-Day itself (6th June 1944). The King forbid it so on what date did Churchill make his first visit to Normandy?
Question 12. Germany surrendered on 7th May 1945. The next day (Victory in Europe Day or VE Day for short) Churchill made another of his famous speeches to the British nation. Complete this extract from that speech: "God bless you all. This is your victory. In our long history, we have never seen a greater day than this. Everyone, man or woman, ..."
Question 13. Churchill's Conservative Party lost a General Election in July 1945 and Labour came into power. Which Labour politician immediately superseded Churchill?
Question 14. In which year did the Conservative Party once again win a British General Election making Winston Churchill Prime Minister for the second time?
Question 15. When Winston Churchill died in 1965 after a long period of ill health he was denied the honour of a full state funeral.