Greatness in tennis cuts across many generations, the sport’s history a pantheon of champions who each excelled and dominated the game in their own special ways. And so, there come those moments when it’s intriguing and even enchanting to travel back and forth across time and envision possibilities—compelling matches that can only take place in our minds.

In this edition of Talking Tennis with Tracy, join Tracy as she ponders a fascinating matchup between two men who’ve each left a major mark on Wimbledon: a pair of seven-time champions, Pete Sampras and Novak Djokovic. (Watch below.)