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You Should Know: Mind the (two-week) gap

Novak Djokovic vs. Kevin Anderson

The Serb and the South African have played three times at Wimbledon. The most recent of those meetings came in the 2018 final, a match won in routine fashion by Djokovic. More interesting by far was their 2015 fourth-rounder, when Anderson won the first two sets in tiebreakers before eventually succumbing 7-5 in the fifth. Anderson also owns a win over Djokovic, 13 years ago in Miami—yes, at 34 and 35, respectively, these guys have been around a while. The 6’8” Anderson has proven, when his serve and forehand are firing, that he can stay with Djokovic. Whether he’ll be able to stay with him for long on Wednesday is another story. Anderson has been through the injury grind the last few years and is currently ranked No. 102. Djokovic, as you know, is No. 1. Winner: Djokovic

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Ons Jabeur vs. Venus Williams

Is there really a player Venus Williams hasn’t faced by now? Yes, there is. The just-turned-41-year-old American will face Jabeur for the first time in the last match on No. 1 Court on Wednesday. That will be later in the day, but it will still be a quick turnaround for Venus, who had to go three sets to win her first-round match on Tuesday. Even more daunting, perhaps, is all the running she’ll likely have to do to track down Jabeur’s changes of pace and out-of-the-blue drop shots, which she employs as often as anyone in tennis. But Venus won’t go down without a fight, that much we know. Winner: Jabeur

A hopeful Tiafoe challenges a call in his win over Tsitsipas.

A hopeful Tiafoe challenges a call in his win over Tsitsipas.

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Frances Tiafoe vs. Vasek Pospisil

U.S. fans will be wondering: Can Tiafoe follow up his biggest-ever win over Stefanos Tsitsipas? It won’t be easy; Tiafoe himself describes the 6’4 Pospisil as a “problem.” The 31-year-old Canadian is currently ranked 65th, well below Tsitsipas, but he has had more success at Wimbledon, where he was a quarterfinalist in 2015 and won the doubles title in 2014. He also has a bruising serve and a two-handed backhand that will presumably be more effective than Tsitsipas’s one-hander was on Monday. Tiafoe and Pospisil have never played at the ATP level, which makes this one tough to call. But Frances is playing too well to stop now, right? Winner: Tiafoe