Kyle Edmund suffered a straight-sets defeat against Denis Shapovalov in the second round of the Cincinnati Masters.
Edmund, representing Britain’s last hope for success in the tournament, was beaten 6-4, 7-5 by the Canadian in one hour, 53 minutes.
Edmund failed to recover in the second set, falling below par on his first service game and giving his opponent an early 2-0 lead.
The Brit fought back and managed to level the score at 4-4, saving a match point at 5-5.
Shapovalov, 19, dominated with a number of impressive backhands and despite needing four match points, ultimately broke Edmund’s serve to advance to the third round.
In the women’s event, meanwhile, Serena Williams lost a second-round thriller against Petra Kvitova.
Former world No1 Williams looked rusty in the first set, struggling to handle the Czech’s booming left-handed serve and never created a break-point opportunity.
The 23-time Grand Slam champion dug deep in the second, thumping serves and blasting returns.
Williams appeared broke Kvitova at the start of the deciding third set but Kvitova elevated her service game and was defensively resolute to seal a 6-3, 2-6, 6-3 and set up a third-round clash with Kristina Mladenovic.
France’s Mladenovic defeated qualifier Viktoria Kuzmova 6-3, 6-0, while her sixth-seeded compatriot Caroline Garcia beat Victoria Azarenka 6-4, 7-5.
