Just before 7am a car left Clarence Town Road, hit an embankment, launched into a power pole and impacted roof first.
A nurse on her way to work was first on the scene and cared for the 17-year-old male driver until rescuers arrived.
The driver was airlifted to John Hunter Hospital with multiple injuries, by the Westpac Rescue Helicopter.
Just after nine, another vehicle left Paterson Road near Woodville and hit a power pole.
The female driver of that vehicle died at the scene, a 27-year-old female passenger has been taken to John Hunter Hospital.
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