The collision was reported to the emergency services at 10.20pm on Sunday 6 September on Forest Head Lane, near Harrogate Golf Club.
It involved two vehicles – a blue Volkswagen Polo and red Ford Focus, both travelling in the opposite direction.
The driver of the Polo, a 29-year-old man from the Knaresborough area was taken to Leeds General Infirmary with multiple serious injuries.
The driver of the Focus, a man in his forties from the Ilkley area was taken to Leeds General Infirmary with serious abdominal and pelvic injuries. A woman passenger in the Focus, aged in her thirties was taken to Harrogate District Hospital with minor injuries.
Any witnesses are asked to call 101, select option 2 and ask for Harrogate Roads Policing Group. Please quote reference 12150157451 when passing on information.