It was a Wednesday to forget for some of the biggest names in women’s tennis at the ongoing Italian Open in Rome as second seed Naomi Osaka and tennis legend Serena Williams both falling to shock second round defeats in the clay-court warm-up ahead of Roland Garros.

Williams who was playing the 1000th WTA match of her career lost on her return after nearly three months away to Nadia Podoroska.

The 39-year-old eighth seed fell 7-6 (8/6), 7-5 in under just two hours to the 44th-ranked Argentine, a surprise semi-finalist at last year’s Roland Garros.

Podoroska’s win was just the third time she would triumph over a top-10 player, all in the last eight months.

Williams, a four-time Rome winner and 23-time Grand Slam champion, had not played since her semi-final defeat in the Australian Open this year.

The early exit is a blow three weeks before the French Open in Paris on May 30 where the American continues her bid to equal Australia’s Margaret Court’s record of 24 Grand Slam trophies.

American Williams has now lost 149 times with 851 wins over the course of a WTA career covering 1000 matches.

Podoroska next meets Croatia’s Petra Martic, who earlier beat France’s Kristina Mladenovic 7-5, 6-3.

Elsewhere, Japan’s Osaka crashed out of the Italian Open after a 7-6 (7/2), 6-2 second round defeat to American Jessica Pegula.

The four-time Grand Slam winner, seeded second in the Italian capital, had received a first-round bye, but was unable to find her way back into the match after losing the first-set tie-break to her 31st-ranked opponent.

Osaka was playing just her third tournament since winning the Australian Open in February and also exited in the second round in Madrid earlier this month.

Osaka, the reigning US Open champion, has seven career hard-court titles, but has never managed to lift a clay-court trophy.

Pegula, 27, who reached the Australian Open quarter-finals, will next play either 33rd-ranked Russian Ekaterina Alexandrova or American 13th seed Jennifer Brady.