Rose Windross originally began as a singer–songwriter on the UK reggae scene. She recorded her first album, Just Rose, on the Ital Records label when she was still at school.
Windross both wrote and recorded Soul II Soul's first single "Fairplay" for Jazzie B, which is featured on the album, Club Classics Vol. One. In the U.S., although the single was pressed, "Fairplay" was never officially released as a single there, but it appeared on the B-side to the single "Feel Free".
In 1996 she performed vocals on Dpd's (one of Dillon & Dickins's aliases) cover version of "Sign Your Name" by Terence Trent D'Arby which was released on Higher State's sublabel 99 North.
Windross joined her brother Norris Windross in 1999 to launch W Records through his own booking agency, Da Boss Entertainments.