(1) Novak Djokovic vs. Philipp Kohlschreiber
Djokovic and Kohlschreiber will be squaring off for the eighth time in their careers when they clash in the Wimbledon first round on Monday. Kohlschreiber upset Djokovic 6-4, 6-4, 6-4 at the French Open in 2009, but the Serb has since won five in a row and he is now 2-1 at the German’s expense in Grand Slam competition. The two veterans faced each other three times in 2014, with Djokovic getting the job done in Rome, at the U.S. Open, and on the indoor hard courts of Paris.
Kohlschreiber just barely missed out on a seed at No. 33 in the world and as an extremely dangerous opponent he will not be underestimated. The 31-year-old also had to go up against Roger Federer in the Halle first round earlier this month and the Swiss just barely survived 7-6(8), 3-6, 7-6(5). Kohlschreiber preceded that with a quarterfinal showing in Stuttgart, so has plenty of grass-court practice under his belt. Djokovic, on the other hand, has not played since Roland Garros. It should not take long for him to get comfortable on grass as the defending champion and two-time winner at the All-England Club. Count on the top seed, who is 41-3 on the season, passing this stern test without too much trouble.
Pick: Djokovic in 3 losing 11-14 games
Teymuraz Gabashvili vs. Alexander Zverev
This will be Zverev’s first-ever appearance in the main draw of a Grand Slam. The 18-year-old German previously failed in qualifying attempts at the three most recent majors, but he gained direct entry this time around thanks to having surged to No. 76 in the world. Zverev owns six of his 10 career ATP-level match victories this season and he is coming off a third-round performance on the grass courts of Nottingham.
Up first for the youngster on Monday is Gabashvili in what will be their only head-to-head meeting to date. Gabashvili is utterly averse to grass, which explains why he went back to the Challenger level to play one event on clay and another on hard courts in between the French Open and Wimbledon. The 30-year-old Russian is 1-6 lifetime in main-draw action at the All-England Club. He is a modest 8-12 at the ATP level this year after making a run to the fourth round at Roland Garros. Grass will not treat him so kindly.
Pick: Zverev in 4