The crash was reported at 1:09 a.m. north of Brick Granary Road and the northern end of Argos Corner Road.
The man killed was from Dover but police withheld his name pending notification of next of kin.
Police said witnesses saw a 2010 Mercedes C30 being driven recklessly and it failed to stop for a stop sign on Johnson Road at Route 1.
The car continued across the highway and into a field where it spun around, then returned to Route 1 (Coastal Highway) and traveled south in the northbound lanes.
The left front of the Mercedes struck the left front of a northbound 1999 Volkswagen Passat in the left lane.
The Volkswagen rolled onto its roof and slid off the east side of the road at a wooded area.
The Mercedes spun around and came to rest in a grassy area on the west side of the road.
The Passat’s driver was pronounced dead at the scene. Police said he had been wearing a seat belt.
The driver of the Mercedes, a 53-year-old Milford man, suffered injuries that police said were not life-threatening. He was taken by ambulance to a hospital. Police withheld his name pending notification of next of kin. He had been wearing a seat belt.
Police said they are still investigating and no charges have been filed.
Northbound Route 1 was closed about five hours.