Two people were sent flying over a stone wall after a car veered onto a footpath in Pyrmont just before 5pm on Tuesday.
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The two men were flung five metres into the air by the car's impact, witnesses said.
Both victims were treated by paramedics and taken to hospital. One of the men, believed to be in his 20s, was taken to the Royal Prince Alfred Hospital in a critical condition, police said.
The other man, whose age is unknown, was taken to St Vincent's Hospital in a serious condition, police said.
"The car collected them and they went flying over the wall. That's how hard they were hit," said a witness, Ray Leary, who was across the road at the time.
The badly-damaged Nissan Micra came to a stop in front of the stone wall, behind the Australian Maritime Museum. It had veered off Murray Street onto the footpath, witnesses said.
One witness said the driver appeared to have lost control of her car as it came around the bend.
The female driver was uninjured. She was taken to the Royal Prince Alfred Hospital for mandatory blood and urine testing and was expected to be released after precautionary medical checks, police said.
Police confirmed they were called after reports of an accident at 4.50pm.
Police spoke to witnesses at the scene to try to piece together what happened.
The Crash Investigation Unit will examine the circumstances surrounding the incident.