The repeated break-ins occurred on the west side of Interstate 95 between April 5 and April 27.
Some surveillance video shows a masked individual wearing gloves, shattering windows or doors with an object before climbing inside. Business owners and residents say they fear the crime spree may escalate.
One video captures a suspect throwing a brick through the window of Gino's Pizza on Lancaster Avenue on Monday, then ramming their body through the broken glass.
Co-owner Hamdy Saif said the restaurant was hit twice.
"Two times in the same week, this is a bad sign," Saif said.
He said the suspect stole $250 from the register and fled within seconds. Saif later paid $1,400 to repair the window. The repeated break-ins left him so concerned that he stayed overnight at the shop.
"Last night I sleep here in store," he said. "I don't lock the door. I keep it because actually I wait for him... You should protect yourself, your wealth and your money and your business."
Police confirmed at least 11 reports of burglaries or attempted burglaries in the area during the three-week span. A Liberty Gas station on West Fourth Street was also targeted more than once.
"I don't like something to happen for me or for someone else," Saif said.
Another video shows an attempted break-in at Walt's Chicken Express on North Lincoln Street. In that case, the suspect threw a brick and tried to kick down the door before falling and running away.
Wilmington resident Lester Brice said the incidents have left neighbors uneasy.
"Mad because we don't know if they're going to break into our house," Brice said.
John Delaney said he was working upstairs when he heard a commotion at Walt's Chicken Express.
"By the time I came down, the window was all smashed in," he said.
Detectives are now working to determine whether the incidents are connected.
"I hope they catch them, and I hope someone out there who saw that video knows who that person is and cares about the patrons and the small businesses and stuff like that to come forward and say, yes that's this person - and that will help all of us out," Delaney said.
Business owners say they are increasing security while police continue gathering evidence. Authorities are asking anyone with information or video to contact Detective Joran Merced at (302) 576-3637 or joran.merced@cj.state.de.us.
You can also contact Wilmington Police at (302) 654-5151 or submit tips anonymously through Delaware Crime Stoppers at 1-800-TIP-3333 or online.