Nuno Borges vs Brandon Nakashima — R16 — Cincinnati Open

Two match points slipped away in the second-set tiebreak, and Nakashima answered by refusing to give the set back on serve: 15 holds from 15 across the afternoon, with the four break points Borges mustered — all of them crammed into the decider — turned back one by one. The one swing he needed in the third came in game 4, a break for 3-1, propped up by 27 aces to the Portuguese's eight. Borges matched him error for error at 36 apiece and still finished 14 points light. Two hours and 13 minutes of it books a Cincinnati quarterfinal, with Medvedev already behind him this week.