Winners of The Deadlys Awards 1999, the awards were an annual celebration of Australian Aboriginal and Torres Strait Islander achievement in music, sport, entertainment and community.

• Excellence in Film or Theatrical Score: Tiddas & Alister Jones: My Island Home
• Outstanding Contribution to Aboriginal Music: Coloured Stone
• Most Promising New Talent: Rochelle Watson
• Male Artist of the Year: Jimmy Little
• Female Artist of the Year: Leah Purcell
• Album Release of the Year: Frank Yamma & Piranpa: Playing with Fire
• Band of the Year: Yothu Yindi
• Single Release of the Year: Jimmy Little: "The Way You Make Me Feel"

• Aboriginal Broadcaster of the Year: Rehanna Coulthard 5UMA

• "Deadly Winners 1999". Vibe. Retrieved 28 August 2020.