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Osaka was the first to leave in the afternoon 6-4 and 6-2 in the afternoon in front of Czech Katerina Siniakova before Williams fell to American Sofia Kenin 6- 2 and 7-5 in a dramatic competition in the evening.
Williams was short of games for the opening of the French Open, scoring just three goals after his rich Australian Open race, which ended with an ankle injury in a quarter-final defeat .
Sick, but more recently, a knee injury kept the winner of the 23 major tournaments on the sideline.
However, all tournaments in which the 37 year old player plays can be won. And when Williams recovered from a set and collapsed to lead his rival to 35th place, 5-4 in the second set, few people would have bet against it.
His sleek and powerful service was starting to snap and the 10th seeded had fans on court Philippe Chatrier behind her, especially since Kenin had contested several line calls.
But his 20-year-old enemy, born in Moscow, stuck to it and lost 6-5 in a match that began with Williams' long mistake on a forehand with Kenin failing.
Williams still had a chance but sent a wide forehand to the break point. Then, on a second point of match, his reverse sailed a long time.
Meanwhile, Osaka admitted that the French Open was too difficult to handle.
The world No. 1 has seen becoming the first player since its idol Williams in 2015 to claim the end of three major tournaments.
Different feeling
"Ultimately, I think this tournament has had a different feeling from the other Grand Slam tournaments, or all the other Grand Slams I've played, because I usually find it very liberating and fun all the time, "Osaka told reporters.
The fatigue that Osaka said feeling against Siniakova could have been the result. And she suspected that the headaches she had experienced earlier during clay tennis were due to stress.
Nevertheless, his level of disappointment at his exit was off the charts.
"It would go from one to ten and I'm like a 100 now," said Osaka.
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When, before the tournament, Osaka had declared that she was looking for a grand slam – the last one performed by Steffi Graf in 1988 – this could have been interpreted as a foolish comment or at least as a long-term goal.
Osaka is still only 21 years old.
Thinking about the slam calendar year
But she clearly focused on doing it this year, which she called a mistake.
"I think I was thinking too much about this calendar," Osaka said. "For me, it's something I've always wanted to do, but I think I have to think of it as if it had been so easy, everyone would have done it.
"I just have to continue to train hard and get myself able to do it again with hope."
Osaka adapts to clay, but it's a quick study, as evidenced by a 7-1 record at the surface this season by entering the French Open.
After all, Osaka managed to fill their deficits in the first round against Anna Karolina Schmiedlova and in the second round against fellow Grand Slam champion Victoria Azarenka.
It was as if his victory over Azarenka could trigger a sparkling race, but that was not the case.
Siniakova, 42nd in the standings – the No. 1 in doubles – played in the juniors and for her country in the Fed Cup final last year against the United States.
The 23-year-old tried her luck by converting three of the six break points, while Osaka scored a 0 for 7, all in the first set. She was also tidy, while Osaka made 38 non-forced mistakes.
When Osaka made a point error, Siniakova entered the fourth lap of a major lap for the first time and won a first win against a No. 1.
Halep, cruise Djokovic
Siniakova defeated reigning French champion Simona Halep in China two years ago. On Saturday, Halep defeated Lesia Tsurenko in an hour, 6-2, 6-1, after three badists in her first two outings.
Men's No. 1 Novak Djokovic, three-time major winner Stan Wawrinka and fifth seed Alexander Zverev also progressed in warm, sunny conditions.
Djokovic beat the Italian qualifications, Salvatore Caruso, 6-3, 6-3 and 6-2. He has not given up the set yet – nor is he approaching it.
The Serb's own chances of finishing a grand slam of his calendar year are still valid and if he wins the title, Djokovic would hold the four major tournaments for the second time in his career.
Wawrinka, winner in the 2015 final, won his 500th career victory with a win over Grigor Dimitrov 7-6 (5), 7-6 (4) and 7-6 (8). They were forced to leave the field due to the darkness after two innings on Friday on Court 1.
Wawrinka – who finished 6-2 tied in the final – also won a career grand slam with wins over Dimitrov.
Switzerland will meet fourth-seeded Greek Stefanos Tsitsipas in a much-anticipated one-handed backhand battle on Sunday.
The five sets are not a surprise for Zverev at Roland Garros. He advanced to 5-0 by beating Monte Carlo finalist Dusan Lajovic 6-4, 6-2, 4-6, 1-6, 6-2 one year after crossing the distance in Paris.
Zverev's German compatriot, Jan-Lennard Struff, won the longest match of the day in four hours and 22 minutes, overturning 13th seed Borna Coric (4-6, 6-1, 4-6, 7). -6 (1) and 11-9
Coric barely went 4-20 on breaking points. When he broke at 6-6 of the fifth, he was immediately broken.
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