R Kelly has appeared in court to plead not guilty to 11 charges of sexual abuse, including four counts that carry a maximum prison sentence of 30 years.
The singer stood with his hands folded in front of him during the short hearing at Cook County court in Chicago.
After the appearance on Thursday, his defence attorney Steve Greenberg said: "It's tough. Everything is against him."
The new charges come on top of the 10 counts Kelly was originally charged with in February, but relate to one of the same women.
They include four counts of aggravated criminal sexual assault, which carry the maximum 30-year sentence.
When Judge Lawrence Flood asked if the singer understood the charges, he replied: "Yes, sir."
He then left the court without speaking to reporters.
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Mr Greenberg said afterwards that he did not want to speculate as to why prosecutors brought the new charges.