It happened just after midnight along the 5500 block of Market Square.
According to police, the 39-year-old victim and his girlfriend were parked in a white Cadillac when they were approached by an unknown man who told them they had to leave.
The couple drove away, but returned 30 minutes later.
That's when police say someone approached the Cadillac from behind and fired numerous rounds, hitting the man in the face.
The victim was able to drive a short distance to the intersection of Germantown Avenue and Collum Street, where he flagged down a police officer.
He was taken to Albert Einstein Medical Center in critical condition. His girlfriend was not injured.
No arrests have been made, and no weapons have been recovered.
Anyone with information is asked to call the Philadelphia Police Department.
Tips can be submitted anonymously by calling 215-686-TIPS (8477).