After Vista Judge Blaine Bowman took the verdicts, he sent the panel back to the jury room to continue deliberating on the remaining counts before breaking for the day.
A 77-year-old woman who went to the same gym as Winslow in the beach community of Carlsbad said he committed lewd acts in front of her, including touching himself, while Winslow was free on $2 million bail in February.
Winslow had rape and kidnapping charges filed against him a year ago.
Winslow was arrested in June 2018 on suspicion of kidnapping and raping the hitchhiker and the two separate 2018 indecent exposure charges. On Monday, he was found guilty of raping one woman.
The verdicts follow a roughly three-week trial that saw all five accusers testify and the prosecutor refer to Winslow as a sexual predator.
A 54-year-old hitchhiker said he drove her to an Encinitas shopping center parking lot and raped her in his Hummer in March 2018.
A 57-year-old woman said he exposed himself to her that summer while she tended to her garden. "Kellen Winslow took from these women again and again and again". Following his highly publicized arrest, Jane Doe 4 subsequently came forward to allege that he raped her in 2003 at a home in Scripps Ranch, when she was 17 and he was 19.More news: Mexico given 45 days to curb migrant flow to US
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Jurors acquitted Winslow of a second lewd conduct charge during the fifth day of deliberations in San Diego County Superior Court, according to a video of the courtroom proceedings.
According to the same report, the jury has been ordered to return Tuesday to try to come to a conclusion on the remaining eight charges against Winslow.
The five women testified they didn't know about Winslow's career when they met him.
"Lightning doesn't strike twice, let alone five times", Owens said during his closing argument to the jury.
"Don't take strong parts of one case to fill in the gaps of the weaker (case)", defense attorney Marc Carlos told the jury.
Defence lawyers also said the sex was consensual and that Winslow had cheated on his wife repeatedly with no-strings-attached sex.