FourFourTwo's Dating Game, 13/11/25: Don Carlo's coronation
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Welcome to another edition of FourFourTwo’s Dating Game, the daily test of your football chronology. Today, we're not just looking for a date; we're hunting for the year that launched the legendary managerial career of one of football’s greatest minds: Carlo Ancelotti.
How to play FourFourTwo’s Dating Game
Carlo Ancelotti is now famously the only manager in history to have won the Champions League five times (and counting). But every legend has a starting point, and that's the historical moment we're challenging you to find. The question for today's puzzle is simple: In what year did Carlo Ancelotti first win the Champions League as a manager?
Your goal is to enter the four-digit year (YYYY) that Don Carlo first got his hands on the trophy, back during his initial, hugely successful spell at Milan. It was a victory that cemented his status as an elite coach and was the precursor to the record-breaking run he is still on today.
FourFourTwo's Dating Game is your simple, daily challenge. You have six attempts to guess the correct four-digit year. The stakes are high, but the mechanics are clean and familiar: enter your four-digit year and the system will instantly analyse your submission.
Every digit that is correct and sitting in its perfect place will light up bright green, those correct but in the wrong place will show up orange. Use the feedback from each of your guesses to guide your next attempt, zeroing in on that pivotal year in Ancelotti’s history. Do you have the chronological chops to solve this?
Once you've tried to conquer this challenge, don’t forget that FourFourTwo is the ultimate destination for every kind of football quiz. We pride ourselves on having an inexhaustible supply of the beautiful game’s most interesting facts and challenging trivia, all powered by Kwizly.
We drop new challenges every single day, so whether you’re warming up with the Dating Game or delving into the archives with our Friday Football Quiz or the mind-bending Weekend Crossword, your quiz fix is guaranteed. And for those who want the trivia beamed directly to them, make sure to sign up for our newsletter to get the latest quiz announcements and challenges delivered straight to your inbox.
The best features, fun and footballing quizzes, straight to your inbox every week.

Mark White is the Digital Content Editor at FourFourTwo. During his time on the brand, Mark has written three cover features on Mikel Arteta, Martin Odegaard and the Invincibles, and has written pieces on subjects ranging from Sir Bobby Robson’s time at Barcelona to the career of Robinho. An encyclopedia of football trivia and collector of shirts, he first joined the team back in 2020 as a staff writer.
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