Nakashima became the seventh player from the United States to book a spot in the third round of the grasscourt Grand Slam this year with an eighth spot guaranteed as Maxime Cressy and Jack Sock clash in an all-American battle. Top-ranked American Taylor Fritz, John Isner, Jenson Brooksby, Tommy Paul, Steve Johnson and Frances Tiafoe are the others to have reached that stage -- the most at a Grand Slam since the 1996 U.S. Open and the most at Wimbledon in 27 years. The 20-year-old Nakashima, ranked 56th in the world, hit 22 winners while limiting his unforced errors to 14 to defeat Canadian left-hander Shapovalov. "It felt amazing out there. To play against such a high-level player on one of the biggest stages, it doesn't get much better than that," Nakashima said after his win. "With each match I think my game is progressing in the right direction.