Prosecutors did not immediately say whether they would retry the eight undecided charges but agreed to return to court Friday to discuss that option and possibly set a new trial date.
Winslow, who played for Cleveland, Tampa Bay, New England and the New York Jets, currently faces up to nine years in prison and must register as a sex offender.
The jury on Monday found him guilty of an attack last year on the homeless woman in his picturesque beach community of Encinitas, north of San Diego. Jurors also convicted him of two misdemeanors - indecent exposure and a lewd act in public - involving two other women.
The 35-year-old former tight end - at one point one of the highest paid in the NFL - could face up to life in prison if he is retried and convicted of raping all three women.
After the San Diego County Superior Court sent the jury home Tuesday, prosecutor Dan Owens told reporters the majority of the 12 jurors believed Winslow was guilty of raping more than one woman.
"Ten jurors did feel very strongly that he had committed forcible sexual offenses against more than one victim," he said. "That would lead to a lifetime prison term and that would be another factor that we would consider very strongly in determining how to proceed with the case."
Winslow's attorneys indicated they want him to be sentenced after the case is retried and that they plan to appeal the convictions handed down Monday.
Defense lawyer Emily Bahr said Winslow was "shocked by that verdict" as was his family, including his father, former Chargers icon and Hall of Famer Kellen Winslow, who sat behind his son every day of the trial.
"They're upset of course, disappointed by that outcome but they know that the team is going to move forward and continue to fight the case," she said.
The jury found him not guilty of one count of a lewd act.
The jury of eight men and four women told the judge they were hopelessly deadlocked on the other eight charges after they deliberated for four days.
All five women testified during the trial. Winslow did not take the stand.
Defense attorneys said the sex was consensual and pointed out inconsistencies in the accusers' testimonies. They also argued the women invented the allegations to prey on the wealth of Winslow, who reportedly earned over $40 million during his 10 seasons with the NFL.
The five women testified that they didn't know Winslow was famous when they met him.
Prosecutors said Winslow felt empowered by his fame to abuse the most vulnerable.
The homeless woman in Encinitas, who was 58 at the time, testified that he befriended her and attacked her next to his vehicle after inviting her for a coffee in May 2018. While the jury found him guilty of raping her, they remained deadlocked over a sodomy charge.
If the case is retried, she could be called to testify again, which could mean the next jury could learn of the conviction as it weighs the other rape cases.
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 while she tended to her garden in May of 2018. The jury found him guilty of that charge Monday.
After news of the attacks broke, a woman came forward and said Winslow had raped her when she was a 17-year-old high school student in 2003. He was 19 at the time and had come home from college for the summer.
A 77-year-old woman who went to the same gym as Winslow in the nearby beach community of Carlsbad said he committed lewd acts in front of her while Winslow was free on $2 million bail in February. The jury found him guilty of touching himself in front of the woman while she exercised, but not guilty of committing a lewd act in front of her on a separate occasion in the gym's hot tub.
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