The attacks happened minutes apart early Tuesday morning.
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Action News spoke to the male victim after he was released from the hospital later Tuesday morning. He asked not to be identified.
"When they were coming, I thought they were cops," he told Action News.
But the 29-year-old victim soon realized these were no police officers.
It was around 12:40 a.m., and he had just walked onto the 5000 block of Griscom Street in Frankford when he says he first noticed a white Chevy Impala.
"Then they make a reverse, and they came out of the car," the victim said. "Three guys, one with a shotgun, two with two guns."
Police say a fourth man served as getaway driver. They were all wearing dark clothing, gloves and ski masks.
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"They were, like, 'Give me everything you have!'" the victim said. "And I said, 'I don't have nothing.' I'm homeless, you know? They hit me with a shotgun in the face and everything, they threw me on the floor. They took everything, and when they were going to leave, they shot me."
The man went to Aria Jefferson Health's Frankford Campus facility in stable condition.
The hospital notified police.
While police were interviewing him, an 18-year-old woman was being treated for facial injuries in the same emergency room.
She told police she was walking from SEPTA's Frankford Transportation Center around 12:15 a.m. and was about a block away on Frankford Avenue, when police say a man grabbed her neck from behind and struck her in the head with a handgun.
They took her wallet, then started punching and kicking her in her ribs as they demanded money. The victim curled up on the highway to protect herself.
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The men fled, only to strike again 25 minutes later, police say.
"We believe these perpetrators are responsible for these two robberies," said Philadelphia Police Chief Inspector Scott Small told Action News early Tuesday morning.
Word of the violent robberies troubles nearby residents, though some say they aren't surprised.
"I just walked in at 11 o'clock... yesterday evening," said Chuck Gatlin. "I'm thinking they could have got me coming from 7-Eleven."
"We have children on this block," said Jeanette Schauland. "What are we going to do when we send them to the store? Are we going to worry about them getting robbed or shot?"
The search for the four suspects continues.