The rape Winslow was found guilty of involved a 58-year-old homeless woman in 2018. Jurors also found him guilty of one count of lewd contact with the victim identified as Jane Doe No. 5, but they found him not guilty of a second count of lewd contact the same woman.
The two other counts of rape involve a 54-year-old hitchhiker and an unconscious teenage girl in 2003.
Jury deliberations started June 5.
The accusers included a hitchhiker and a homeless woman who said they'd been raped in his SUV, and a woman who said a stranger exposed himself in her yard.
"Kellen Winslow took from these women what he wanted". Jurors went home less than an hour later and were ordered to resume deliberating Tuesday.
'Kellen Winslow took what he wanted; he took what he wanted not from one, not from two, but from three women, ' Owens said during the trial, as quoted by Cleveland's NBC affiliate. "Kellen Winslow took from these women again and again and again".
After that season, Winslow chose to forgo his senior season at UM and declared himself eligible for the 2004 NFL Draft.
All five women testified during the nine-day trial.
"This defendant is motivated by pure, unadulterated depravity for his own sexual purposes", Deputy District Attorney Dan Owens told the jury during closing arguments.
Noting the number of accusers, the prosecutor said: "Lightning certainly doesn't strike twice - let alone five times".
Winslow's attorneys say that the alleged incidents were either consensual or never occurred.
Winslow was initially charged last summer with raping Jane Doe 1 and 2 in Encinitas in early 2018, as well as exposing himself to Jane Doe 3 in her yard.
A judge revoked his bail in March after police accused him of lewd conduct involving a 77-year-old, jail records show.