Police are appealing for information following the crash which happened at around 2.30pm on Friday, June 4.
The crash involved a dark green BMW Z3 and a red Hyundai i10 on the A167 near Oak Tree Hill, Brompton.
The BMW was travelling northbound towards Darlington and the Hyundai in the opposite direction when the crash happened.
The male driver of the BMW, who was from the Northallerton area, was sadly pronounced dead at the scene.
The driver of the Hyundai was taken to hospital for treatment, but later released.
North Yorkshire Police want to speak to anyone who witnessed the crash or saw either vehicle prior to contact them on 101 quoting reference 12210132205.