Investigators say they are working under the premise that these cases in the Mayfair section of the city are related.
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Police were called just before 4:30 a.m. Monday in the 4600 block of Loring Street near Ditman Street.
Police say a 19-year-old man was shot once in the head.
He was pronounced dead at the scene.
Approximately three hours earlier, someone called 911 after hearing gunshots on the 4500 block of Bleigh Avenue near Jackson Street.
Police say a man in his 20s was found in a rear driveway with a gunshot wound to the head and right leg.
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He died of his injuries at the scene, police say.
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Mayfair residents said the double homicide has left them on edge.
"It's not safe around here at all," said Antonette Sexton.
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"Violence is never the answer but don't kill," said Shayla Jones, adding, "You're not just taking it from them, you're taking it from the family too."
Police are looking through surveillance video in hopes of finding the shooter.
The names of the victims in both cases are not yet known.
These shootings ended a violent weekend in Philadelphia which saw at least 18 people shot, six of whom were fatally wounded.