The state wanted to show a pattern of sexual criminal misconduct by Winner, but late Friday afternoon a judge severely limited that plan.
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Winner is facing multiple felony charges in connection with sexual assaults on four women between 2009 and 2015, and prosecutors said the 46-year-old raped many other women going back more than 15 years -- cases too old to charge.
Prosecutors have called Winner "a real and present threat to the physical safety of any woman" and said they wanted to use evidence of nine other uncharged attacks against him during the prosecution.
Friday Cook County Judge Carol Howard dashed the state's grand plan, nixing evidence in five of the previous, never-charged allegations. Howard ruled that at trial the state will only be allowed to present evidence from the alleged incidents involving four additional women.
"The judge is a fair judge she listened to the evidence she did the right thing," said Steven Weinberg, Winner's attorney.
The most significant hit to the prosecution on Friday was Judge Howard's refusal to allow evidence from an alleged rape that prosecutors consider most similar to a 2009 attack, for which Winner is charged.
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The judge determined that accusations Winner tried to strangle the victim in that uncharged attack would make it too prejudicial.
Last year, Winner tried to jump an I-Team crew outside the criminal courthouse. Friday, he was more restrained, declining comment and he remains free on bond.
Friday's ruling does clear the way for 2001 Winner victim Lesley Barton to testify, if prosecutors choose, she told Glenview police that the tanning salon owner had raped her but the charge was plea bargained down and Winner was sentenced to two years' probation.
"I am just so sorry that I couldn't stop him," Barton told the I-Team in an interview last year. "I told everyone what he was going to do. I knew this was going to happen. I prayed it didn't."
Prosecutors asked the judge to order Winner to surrender the pass code to a cell phone that police seized at the time of his arrest. Authorities contend there is evidence on the phone, including photos, but they can't unlock it. Winner refused to give up the phone, claiming the Fifth Amendment.