Grigor Dimitrov’s French Open hopes bit the dust as the fourth seed was outplayed by Spanish veteran Fernando Verdasco in the third round on Friday, the Bulgarian losing 7-6(4) 6-2 6-4.
Dimitrov was pushed to five sets by American Jared Donaldson in the previous round and once he failed to convert four set points in the 12th game of the opener against Verdasco and lost the ensuing tiebreak, he looked flat.
The aggressive left-handed Spaniard broke twice in the second set and although he allowed Dimitrov back from 4-2 in the third, he broke again to claim his third career win against the 27-year-old.
Verdasco has now reached the last 16 in Paris for the seventh time and will hope to finally break through that barrier having fallen at that stage on six occasions.
In other early action on Friday, American 13th seed Madison Keys overcame a second-set wobble to beat Japan’s Naomi Osaka 6-1 7-6(7) and reach the last 16 for the second time.
A match between two of the biggest hitters on the WTA Tour failed to really catch fire on a cool and half-empty Suzanne Lenglen Court with Keys helped on her way to the first set by a succession of wild errors from Osaka.
Keys broke for a 3-1 lead in the second set and looked to be closing in on a straightforward victory when 21st seed Osaka suddenly found her range and levelled the set.
Osaka’s mini-revival looked to have fizzled out when she dropped serve with a double-fault at 4-4.
Keys squandered a match point in the next game, however, and the 23-year-old US Open runner-up looked increasingly tight as the set moved into a tiebreaker.
Osaka led 4-1 but Keys dragged it back to 4-4 with a searing backhand pass but faced a set point at 5-6 and needed some superb defence to fend off the fired-up Japanese.
Keys saved another set point at 6-7, this time with a booming first serve. She then wrong-footed Osaka to bring up a second match point and was relieved as her opponent coughed up another double-fault to end the contest.
She will face either fourth seed Elina Svitolina of Ukraine or Romanian Mihaela Buzarnescu next.
Keys is one of three Americans to reach the third round with Sloane Stephens, who beat her in the Flushing Meadows final last year, and three-time champion Serena Williams also in the hunt.