Wimbledon second Monday expert picks, including Nishikori vs. Gulbis and Isner vs. Tsitsipas

Ricky Dimon of the Grandstand and Pete Ziebron of Tennis Acumen make their picks for four of the best matchups on the second Monday at Wimbledon. The jam-packed schedule includes Kei Nishikori vs. Ernests Gulbis and John Isner vs. Stefanos Tsitsipas.

(24) Kei Nishikori vs. (Q) Ernests Gulbis

Ricky: Even before Saturday, Gulbis was already the last qualifier remaining in the draw. From completely out of nowhere, the suddenly resurgent Latvian now finds himself in the second week at Wimbledon following a five-set stunner over Alexander Zverev–his third consecutive five-set victory. Nishikori, meanwhile, underwhelmed through two rounds but picked up the pace in a major way and was outstanding in a surprising straight-set rout of Nick Kyrgios. The No. 24 seed is now 4-0 lifetime against Kyrgios and he is 2-0 vs. Gulbis, who has a similar style to that of the Aussie–and a similar mentality, too. This should be a fun one, but in the end Nishikori will likely get too many balls back and wear down the underdog. Nishikori in 5: 3-6, 6-3, 6-7(4), 6-4, 6-3.

Pete: Four years ago en route to a Roland Garros semifinal berth, Gulbis stated that he planned to be world No. 1. Since that time, he has done little to back up the boast. This year, the Latvian had to qualify for the main draw and has actually trailed after the first set in three of the six matches he has played. However, he won 12 of the last 15 games of the match to stun Zverev advance advance to the fourth round. Nishikori yielded just 11 points to Kyrgios in the opening set of their third-round encounter and marched to an impressive straight-set win over the talented Aussie. The Japanese star has reached at least the quarters of all of the majors except for Wimbledon. Somehow these veteran players who have been on the ATP Tour for more than a decade have met only once. Gulbis has gone the distance in each of his three main-draw matches, while Nishikori has been able to win efficiently. This fact will contribute significantly to the end result. Nishikori in 4: 6-4, 6-3, 3-6, 7-6(3).

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(9) John Isner vs. (31) Stefanos Tsitsipas

Ricky: Too many long matches in early rounds have plagued Isner later at Grand Slams. He needed five to beat Ruben Bemelmans in round two, but that was spread across two days and the 6’10” American finished the fifth before it got to marathon status. He also made lightning-quick work of Radu Albot on Friday and will have two days off prior to this one. Isner has not been broken through three rounds and he has been awesome on break points, saving all five he has faced while converting 11 of his 27 opportunities. Big-point and big-match experience may make the difference for Isner over the young but talented Tsitsipas in what is sure to be a competitive contest. Isner in 4: 6-7(4), 6-4, 6-4, 7-6(8).

Pete: Isner, though respectful of his upstart opponent, recognizes the absolute golden opportunity he has to potentially reach a Wimbledon semifinal this year. The service of the lanky American has been nearly immaculate through three matches, hitting 113 aces against only nine double-faults while concurrently serving at a healthy 77 percent first-serve percentage. Should Isner get past the young Greek, he holds a 3-1 H2H lead against probable quarterfinal opponent Milos Raonic. However, Tsitsipas has played solid tennis for the last few months and plans to dig in against Isner and play his fearless brand of tennis. The American will recall how close he was to exiting Wimbledon, saving two match points in his second-round match and will plan to not be anywhere near red alert territory in this match. Isner will hit aces when he needs them. Isner in 4: 7-6(4), 3-6, 7-6(4), 6-4.

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Gael Monfils vs. (8) Kevin Anderson

Ricky: This was shaping up to be the 17th career contest between Anderson and Sam Querrey, and second in as many years in the Wimbledon fourth round. But Monfils had other ideas, as he recovered from a set deficit to pull off an impressive grass-court upset of Querrey 5-7, 6-4, 6-4, 6-2. The Frenchman, who ousted Richard Gasquet in round one, has somehow emerged from a slump to achieve this success on what has to be considered his worst surface. Asking for a fourth win of the fortnight may be too much. Anderson is a proven force on grass who has now advanced to the Wimbledon fourth round four times. His 0-5 record against Monfils is alarming, but they have not faced each other since 2016 and Anderson is a much more confident player now. Grass also helps his chances. Anderson in 4: 7-6(3), 4-6, 6-2, 6-4.

Pete: Monfils is playing after middle Sunday for the first time, in this his 10th appearance at Wimbledon. The Frenchman absolutely owns Anderson, dropping just a single set in their five matches. Meanwhile, the fact that Monfils dispatched Querrey in the third round will have provided him with a comparable blueprint for his round of 16 encounter with the South African. This year marks the fourth time in the last five years that Anderson has reached Manic Monday, but he has stalled each of the previous three times. Expect Monfils to add to the tally in this lopsided matchup, making it six for six. Monfils in 4:  4-6, 6-3, 7-6(5), 6-4.

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(5) Juan Martin Del Potro vs. Gilles Simon

Ricky: This is always a fun matchup and an intriguing contrast in styles. Del Potro leads the head-to-head series 4-3 and four of their seven previous meetings have required deciding sets. The Argentine won an epic five-setter at the 2008 U.S. Open and he needed only three sets in their only previous Wimbledon showdown, but that was a competitive 7-6(8), 7-6(5), 7-5 result in 2011. While the Frenchman’s run to the fourth round has come out of nowhere, Del Potro has been one of the tour’s best players the entire way this season. In the end, the fifth seed will almost certainly have too much firepower for the counter-punching underdog. Del Potro in 4: 6-4, 3-6, 6-2, 6-3.

Pete: Ironically, three of the seven matches played between the Argentine and Frenchman have been contested on grass and Del Potro has won them all. Through three matches at the Championships, Del Potro has not dropped a set and has won 54 of the 80 games he has contested. Simon has finally reached the fourth round of a major for the first time in 30 months. The Frenchman has issued three breadstick sets to opponents and the lone set he has dropped occurred in a tiebreaker. Del Potro has reached the semifinals in two of the last three majors he has played–thus we all continue to wonder what might have been with respect to the injury riddled career of Del Potro. He is aware of the precious time that he is healthy on a tennis court and is eyeing a potential quarterfinal against world No. 1 Rafael Nadal. Del Potro in 4: 7-6(5), 6-7(4), 6-4, 7-5.

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