Two men in their 50s had to be freed from a crashed Ford Focus by firefighters following a collision with a Subaru Impreza.
One of the men was taken to the Northern General Hospital in Sheffield for treatment following the smash on the A619 Chesterfield Road at Hollingwood, Chesterfield.
The other man remains in the Queen’s Medical Centre, Nottingham.
Police are investigating the circumstances surrounding the collision on Monday at 10pm.
Witnesses should call Derbyshire Police on 101.