Crosswords Trivia
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106 free Crosswords trivia questions with answers — trivia quiz, new questions added Oct 2026.
This crosswords trivia quiz covers the newspaper puzzle from its 1913 debut in the New York World to today's apps and tournaments. The easy questions are ones any solver can attempt: what across and down mean, the standard grid size, which day's New York Times puzzle is easiest, what a question mark at the end of a clue signals, and what to call someone who makes or solves crosswords. From there it moves through the history: Arthur Wynne, the 1924 Simon and Schuster book that started a craze, the Times editorial calling it a sinful waste, and the day the paper finally gave in during World War II. The harder end is for cruciverbalists: Torquemada, Ximenes and Afrit and the rules of fair cryptic clues, the Listener puzzle, Leonard Dawe and the D-Day codenames, Margaret Farrar, Will Weng, Eugene Maleska and Will Shortz, the enigmatology degree, the ACPT and Wordplay, the 1996 election-day puzzle, Sondheim bringing cryptics to America, crosswordese, Bletchley Park recruits and the ancient Sator Square. Every answer was checked against encyclopaedia entries on the crossword and its makers before publishing, and the supporting sentence is stored with each question. If you enjoy this one, try our word games, board games and newspaper history quizzes next.
30 of 106 questions with answers and explanations. Play the quiz
Q 01The puzzle now called the first crossword appeared in a Sunday newspaper in 1913 under which name?
Word-Cross
Word-Cross was the heading on that first puzzle, and only later were its two halves swapped round to give the name that stuck.
Q 02What is a person who constructs or solves crosswords called?
A cruciverbalist
A cruciverbalist is, literally, a cross-worder: the term was built in mock Latin from crux, cross, and verbum, word, as a joking translation of 'crossword'.
Q 03What was the trade of Arthur Wynne, who devised the first crossword in 1913?
Journalist
Journalist Arthur Wynne ran his puzzle in the New York World on 21 December 1913, and by the 1920s newspapers across America were printing their own.
Q 04The first crossword ran in 1913 in which part of a Sunday newspaper?
The Fun page
The Fun page was the paper's Sunday puzzle section, and FUN duly turns up as the first word across in that first grid.
Q 05Which cookie turns up in grids so often that it has been dubbed the official cookie of the crossword?
Oreo
Oreo packs three vowels into four letters, so constructors lean on it constantly. In its early New York Times appearances it was clued only as a prefix meaning mountain, never as a cookie.
Q 06Which publishing pair's very first book, in 1924, was the first collection of crossword puzzles?
Simon and Schuster
Simon and Schuster were so nervous about the untested format that they kept the firm's name off the book, issuing it under the alias Plaza Publishing Company. The idea had come from Richard Simon's puzzle-loving aunt.
Q 07Which British newspaper held out against the crossword craze until 1930, years after its rivals had given in?
The Times
The Times had sneered at the American craze in an editorial about a nation enslaved by puzzles, then printed its own first crossword in February 1930. The Sunday Express and Daily Telegraph had run them for years by then.
Q 08What did a 1924 New York Times editorial call the new crossword fad?
A sinful waste
A sinful waste was its verdict on the utterly futile finding of words to fit a prearranged pattern, and it sniffed that solving was not a game at all. The paper then held out for years before printing a puzzle of its own.
Q 09Which event finally pushed The New York Times to launch its own crossword?
The attack on Pearl Harbor
The attack on Pearl Harbor led the Sunday editor to urge the publisher to proceed with a puzzle, since readers would need something to fill bleak blackout hours. The first one ran two months later, in February 1942.
Q 10Who was The New York Times' first crossword editor, serving from 1942?
Margaret Farrar
Margaret Farrar began as a secretary at the New York World, where one of her duties was keeping typos out of the puzzle. She proved so good at it that she ended up running it.
Q 11Which New York Times game, now a stablemate of its crossword, was bought from its creator in 2022?
Wordle
Wordle was built by Josh Wardle, who said the paper's own games had played a big part in its origins. The Times paid a price in the low seven figures, while the other three were launched by the paper itself.
Q 12Will Shortz, NYT crossword editor from 1993, holds the only known degree in what field?
Enigmatology
Enigmatology, the study of puzzles, was a major Shortz designed for himself through Indiana University's individualized program. He had sold his first puzzle to a magazine at 14.
Q 13Which sport does crossword editor Will Shortz play so keenly that he opened a club devoted to it?
Table tennis
Q 21Turn most American crossword grids upside down and the black squares look the same, thanks to which property?
Rotational symmetry
Rotational symmetry means the pattern of black squares survives a half turn. Asked why the rule existed, the first Times crossword editor reportedly replied: because it is prettier.
Q 22What do solvers call obscure words such as ETUI, ERNE and OLEO that turn up far more in puzzles than in life?
Crosswordese
Crosswordese survives because short, vowel-heavy words rescue constructors from tight corners of the grid. Editors still treat too much of it as a flaw.
Q 23Which Grand Inquisitor's name did The Observer's pioneering cryptic setter borrow as a fitting alias for tormenting solvers?
Torquemada
Table tennis became a daily ritual for Shortz, who opened his own club in Pleasantville, New York. By early 2024 he had not missed a day's play since October 2012.
Q 14Which word game was called Criss-Cross Words before it got the name it has today?
Scrabble
Scrabble was Alfred Butts's Criss-Cross Words until a new owner renamed it. Butts set its tile counts by tallying how often each letter appeared on newspaper pages, The New York Times among them.
Q 15What is the standard size of a weekday New York Times crossword grid?
15 by 15
15 by 15 is the daily grid, and a themed puzzle normally fits no more than 78 answers into it. A themeless one is held to 72, so its answers have to run longer.
Q 16Which day's New York Times crossword is the easiest?
Monday
Monday is the gentlest, and the puzzles then get harder each day until Saturday. Solvers use the days as shorthand, so any easy puzzle gets called a Monday.
Q 17The giant Sunday New York Times crossword is not the week's hardest; it is pitched at about which day's level?
Thursday
Thursday is the usual yardstick, though the Times itself says Wednesday or Thursday. The week's real brute is Saturday's puzzle, on a grid about half the size.
Q 18A question mark at the end of a crossword clue usually signals what?
A punning answer
A punning answer is on the way, because the mark warns that the clue should not be taken at face value. Easier puzzles add it as a courtesy, while harder ones often leave it off.
Q 19What does the abbreviation Var. in a clue tell the solver?
The answer is a variant spelling
The answer is a variant spelling, a rarer form of a familiar word such as EMEER in place of EMIR. The tag is the constructor's admission that the usual spelling would not fit.
Q 20Which type of clue is usually the easiest in an American puzzle and a good place to start?
Fill-in-the-blank clues
Fill-in-the-blank clues are the usual way in, because a familiar phrase with a gap all but completes itself. Blank Boleyn, for instance, can only be ANNE.
Torquemada, the first Grand Inquisitor of Spain, lent his name to the poet Edward Powys Mathers, whose Observer puzzles began in 1926. His successor at the paper kept up the joke by signing as another inquisitor.
Q 24Which pen name, taken from a Spanish inquisitor, belonged to the Observer setter who wrote the rulebook of fair cryptic clueing?
Ximenes
Ximenes was the classics master Derrick Macnutt, who borrowed the name of a cardinal who once led the Spanish Inquisition. His rules of fair play are still known as Ximenean principles.
Q 25Which television detective was named after a bank chairman who kept beating his creator in crossword clue-writing contests?
Inspector Morse
Inspector Morse took his surname from Sir Jeremy Morse, the Lloyds Bank chairman who kept winning the Observer clue contests that novelist Colin Dexter also entered. Sergeant Lewis was named after another regular winner.
Q 26Afrit's rule for setters: you need not mean what you say, but you must what?
Say what you mean
Say what you mean was the rule Alistair Ferguson Ritchie, who set as Afrit, laid down in his book Armchair Crosswords. A clue may mislead, but its wording must still lead logically to the answer.
Q 27Which weekly crossword, begun in 1930, has outlived the BBC magazine it is still named after?
The Listener
The Listener crossword began in the BBC's weekly magazine in 1930. When the magazine closed in 1991 the puzzle moved to The Times, where it still runs on Saturdays under its old name and numbering.
Q 28MI5 questioned a Daily Telegraph crossword compiler after his answers included Utah, Omaha and Overlord, codewords for what?
The D-Day landings
The D-Day landings were weeks away when the words appeared, joined by Mulberry and Neptune. The compiler, headmaster Leonard Dawe, was cleared; a former pupil later said boys had picked the words up from soldiers camped nearby.
Q 29Some cryptologists for which wartime codebreaking centre were recruited after doing well in a crossword competition?
Bletchley Park
Bletchley Park gained recruits after the Daily Telegraph ran a contest to solve its crossword in under 12 minutes. Weeks later, the War Office quietly wrote to those who had done well.
Q 30Which Broadway composer is credited with introducing cryptic crosswords to Americans through puzzles in New York magazine in 1968-69?
Stephen Sondheim
Stephen Sondheim set the puzzles for about a year and gave up only when writing the musical Company left him no time. His games-filled home also helped inspire the thriller Sleuth.