Detectives believe both incidents involve an "ongoing dispute," Lt. John Romero told the Los Angeles Times, without offering details.
Jason Lee, a police spokesman, said no one was injured in either incident.
The unnamed suspect was arrested and released after the first crash last Thursday night, Lee said. He slammed his car into the gates again Tuesday, but fled before police arrived. The gates sustained some damage.
Police did not know if Hefner, the founder of Playboy magazine, or his three girlfriends were at home at the time.
Officials at Playboy's corporate offices in Los Angeles and Chicago could not be reached for comment Wednesday night.