West Midlands Ambulance Service received several 999 calls reporting the serious collision at the junction of Patshull Road and Holyhead Road, in Albrighton, at around 12.50pm.
A passenger from one of the vehicles, a man, sustained serious injuries and was rescued from the vehicle by firefighters. He has been airlifted to the Queen Elizabeth Hospital in Birmingham.
Both drivers were assessed by paramedics – with one taken to New Cross Hospital for further treatment.
A West Midlands Ambulance Service spokesman said: "There were three patients in total involved in the collision. A passenger from one car, a man, sustained serious injuries.
"Ambulance staff worked closely with the fire service to carefully extricate him from the car whilst he received treatment for his injuries.
"Once released the man was airlifted to Queen Elizabeth Hospital Birmingham for further trauma care.
“Both drivers had self-extricated from their cars and were assessed by the team of ambulance staff. One driver, a man, sustained injuries not believed to be serious and was treated on scene before he was taken by land ambulance to New Cross Hospital for further treatment.
"The second driver declined assessment.”
Two ambulances, a paramedic officer and two Midlands Air Ambulances – one from Tatenhill with critical care paramedics and the other from Cosford with a critical care paramedic and doctor on board – all attended the scene.