Big fans of Jannik Sinner and Carlos Alcaraz should be able to name all the Grand Slam tournaments they've each won. Diehards might even rattle off all of their Masters 1000 victories, and maybe even their first trophies on the ATP Tour, period.
But can even the biggest Sinner supporters and Alcaraz acolytes name the titles these two titans won before they hit it big, on the ATP Challenger Tour?
Challenger championships don't compare to what these stars would go on to achieve, but they were essential in building confidence and amassing experience. When you haven't yet won Wimbledon, winning an ATP Challenger Tour event for the first time can feel just as significant.
Over the past few months, we caught up with some of the most celebrated Champions in men's tennis—and spoke to them about when their very first triumph, as a Challenger.



!["I arrived the night before and I played against a Top 500 player. And I [had] never won against a Top 500 player," says the now-world No. 1.](https://images.tennis.com/image/upload/t_16-9_768/f_auto/tenniscom-prd/udlyqsxnviwkoba0yokk.jpg)



