It happened around 5 p.m. Tuesday on Sunset Lake Road near Reybold Road.
Rescue crews had to use the Jaws of Life to free both male drivers.
The men, ages 73 and 27, were rushed to the hospital with similar traumatic injuries to their heads and torsos.
Though the 5-year-old girl, who was in the car with the 27-year-old man, was not trapped, she was the most seriously hurt.
The girl is listed in critical condition.
The cause of the crash is still under investigation.