Investigators said the incident happened Friday at about 10:17 p.m. on Emancipation and Wheeler Avenue.
A patrol officer reportedly saw a white pickup truck speeding on Emancipation Avenue when he turned on his lights, according to police.
"It was almost a car chase - sort of," HPD Lt. R. Willkens said.
The driver allegedly turned around and went through side streets, and ended up on Wheeler Avenue.
He then reportedly ran through the intersection and crashed into a convertible, launching the truck onto four parked cars. Police said no one was in those cars.
The man driving the truck was injured but is expected to be OK, according to police. The woman driving the convertible was transported to the hospital in an unknown condition.
"He is in custody. It doesn't appear that the truck was stolen. He does have city warrants. He also has a lengthy criminal history. You name it. He's probably done it," Willkens said.