Getty ImagesIt's claimed Usher paid a celebrity stylist $1.1m (£840,000) after infecting her with a sexually transmitted infection.
Leaked court papers published by Radar Online claim the US singer contracted herpes in 2009 or 2010.
The unnamed woman is said to have been "devastated" and "extremely depressed" after testing positive for the disease.
Usher, 38, was accused of having unprotected sex with the woman while knowing he carried the virus.
He has reportedly told Hollywood Life he feels "embarrassed and horrible" about what happened - but there has been no public statement.
Getty ImagesUsher performs onstage with Pharrell Williams during Gabrielle's Angel Foundation Hosts Angel Ball 2013Real name Usher Raymond IV, he is reported to have dated the woman between 2011 and 2012.
Radar Online also released a photocopy of a cheque for $2,754 (£2,110) which it's claimed the singer issued to cover the woman's medical bills.
Usher is known for hit songs such as OMG, DJ Got Us Fallin in Love and Yeah!
His 2004 Confessions album is one of the biggest selling US albums of the 21st century.
Usher often shares inspirational quotes on Instagram.
Usher is an eight time Grammy Award winner and a former coach on The Voice USA.
He's also credited with guiding Justin Bieber through the early stages of his career.
Getty ImagesHe's also carved out a successful acting career appearing in The Hangover, Fast & Furious 6 and Muppets Most Wanted.
Most recently he starred as boxing legend Sugar Ray Leonard in Hands Of Stone.
See Usher poses next to Sugar Ray.
Genital herpes is a common condition, especially in people from 20 to 24 years old, according to NHS figures.
In 2013, 32,279 people attended a sexual health clinic in England with an attack of genital herpes for the first time.
The herpes simplex virus (HSV) can cause painful blisters - but it is often carried without symptoms.
Even if someone with genital herpes doesn't have any symptoms, it's possible for them to pass the condition on to a sexual partner.
You can get more support about STIs on these BBC Advice pages.
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