As the Miami Open gets ready to wind down, perhaps no lineup of matches represents the past, present and future of the ATP Tour than what’s on tap for Thursday.

In the quarterfinals, Roger Federer—with 20 Grand Slam titles to his name—faces two-time major finalist Kevin Anderson. Federer, who’s won Miami three times amid his 100 career titles, leads their head-to-head matchup 5-1. Anderson’s lone victory was a big one as he rallied from the brink of defeat to stun the Swiss at Wimbledon last year in the quarterfinals.

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The other scheduled match pits two players against each other with one singles title and Grand Slam quarterfinal between them—results that are expected to become a distant memory soon enough.

Denis Shapovalov and Frances Tiafoe, two of the game’s brightest young talents, will face off for the third time in their burgeoning careers. They split their two meetings last year, with the American Tiafoe beating his Canadian counterpart en route to his first title in Delray Beach. Shapovalov turned the tables on Tiafoe in Cincinnati, topping him in a three-set battle.

Anderson carries a 4-1 combined record against the NextGen stars, with his lone loss coming to Tiafoe at this year’s Australian Open. Federer’s 3-0 against Tiafoe, with one of those wins a five-set victory at the US Open nearly two years ago, and has never faced Shapovalov.

Regardless of the final result, the veterans can rest easy knowing the game will be in good hands when they’re gone.

Follow Van on Twitter: @Van_Sias