Japan's Osaka fell to a 7-6, 6-2 defeat to American Jessica Pegula in the clay-court warm-up before the French Open at Roland Garros.
The four-time Grand Slam winner, seeded second in Rome, 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 suffered a second-round defeat in Madrid earlier this month.
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 now face the Russian Ekaterina Alexandrova.
Williams, playing the 1000th WTA match of her career, lost to Nadia Podoroska on her return to action after nearly three months away.
The 39-year-old eighth seed fell 7-6, 7-5 in under just two hours to the 44th-ranked Argentine, a surprise semi-finalist at last year's Roland Garros.
Williams, a four-time Rome winner and 23-time Grand Slam champion, had not played since her semi-final defeat to Osaka at Melbourne Park in February.
World No 1 Ashleigh Barty had no such problems in Rome, sweeping past Kazakh Yaroslava Shvedova 6-4, 6-1.
Days after her surprise defeat in the Madrid Open final to Aryna Sabalenka, the Australian overcame an early break of serve to see off Shvedova, a three-time Grand Slam quarter-finalist making her way back after giving birth to twins.
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