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Of the dozens of matches Jack Sock and Denis Kudla have played, their Friday round of 16 meeting at the Indian Wells Challenger might be the most fascinating one yet. From Masters 1000s, ATP 500s, ATP Challengers, ITF futures, USTA Wild Card Challenges and too many junior tournaments to count, Sock and Kudla, separated in age by just a month, have gone through the ups and downs of life as a tennis player together.

Their games, as well as their personalities, couldn’t be more different. Kudla’s demeanor is typically as level as the trajectory of his laser-like two handed backhand, while Sock’s emotions can rise and fall as quickly as his topspin forehand, which as long he’s breathing, will be one of the game’s deadliest.

But now both players are on the outside looking in, fighting once again on the unforgiving ATP Challenger tour for the first time since 2012, the same place they launched their successful careers. Both have tasted second week Slam success, and both have represented their country in the Olympics. But now each find themselves ranked outside of the Top 100, trying desperately to claw back inside and again enjoy the top tier prize pools.

Match of the Day: Denis Kudla vs. Jack Sock, Indian Wells Challenger

Match of the Day: Denis Kudla vs. Jack Sock, Indian Wells Challenger

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“I’m still getting healthy and still getting reps,” Sock told Tennis.com last fall. “People still like to hate on me even though I’ve only played a handful of events.

When asked if he’s excited to once again show the tennis world what he is capable of, Sock responded, “For sure, my career was a steady rise to the Top 10, that’s in me… it’s not so far away.”

Earlier this week, Sock defeated world No. 42 Ugo Humbert in straight sets, then battled past Evgeny Donskoy, breaking the Russian when down, 6-5, in the third—a match Sock would have lost in the not-so-distant past. On Thursday, Kudla defeated the highly-touted Jannik Sinner, 6-3, 6-7 (4), 6-2, saving 11 of the 12 break points he faced against the 18-year-old.

There are no secrets on the court between Sock and Kudla, and while the conditions definitely favor the heavy-hitting Sock, this match could ultimately come down to nerves and fitness. Both players would tell you it’s just another match, but after all they’ve been through during their careers, this is as special as a round of 16 match at a Challenger will get.

Match of the Day: Denis Kudla vs. Jack Sock, Indian Wells Challenger

Match of the Day: Denis Kudla vs. Jack Sock, Indian Wells Challenger