The incident occured yesterday (Monday 9th March) at 12:08pm.
Police say it happened on the A629 at a roundabout near the junction with Wyvern Road.
Officers say a blue Ford Focus was travelling northbound along the A629 when the driver approached the roundabout.
The vehicle was then involved in a collision with a black Mercedes E300.
The man driving the Ford Focus was taken to hospital with life-threatening injuries.
Police are now asking for anyone who witnessed the collision, or who may have dashcam footage from the area at the time, to come forward.
They are particularly interested in hearing from anyone who may have seen either vehicle before the incident, including their manner of driving.
Anyone with information is asked to contact police by emailing joanne.ollerenshaw@northyorkshire.police.uk or by calling 101 and asking for Joanne Ollerenshaw.
Members of the public should quote the reference number 12260042625 when providing information.

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