Those arrested ranged in age from 22 to 76 and are expected to be charged with a string of Commonwealth offences including false accounting, according to police.
Commander Millen said they were not gang members, but were "legitimately involved" in running the businesses. She described the sting as a "significant blow" to the gang and vowed to "shut down its operations".
"The Comanchero are a group we know have traditionally been involved in violent crimes such as shootings, assaults, arson, drug trafficking and extortion," she said.
"While we investigate those crimes, we also recognise that there are opportunities to target OMCGs in a way that reduces their wealth and effectiveness.
"The public might not be aware they were using a service linked to an outlaw gang and contributing to organised crime.
"The businesses are allegedly used as a front for organised crime activities and money laundering activities.
"The Comanchero also have a range of business enterprises that they themselves are directly involved in, such as gymnasiums, tattoo parlours and brothels, where they haven't undergone the correct licensing, insurance or registration processes."
The sting was one of the largest operations by the force targeting organised crime, according to police.
"The Comancheros won't have an opportunity to expand given the significant disruption strategies we've engaged in today," Commander Millen said.
The dramatic raids were part of a national day of action against the Comanchero and businesses allegedly linked to the group. They come after bikie boss Mahmoud "Mick" Hawi was slain as he sat in his luxury car outside the Fitness First gym in Rockdale on February 16. The 37-year-old was shot multiple times and died.
Security cameras captured two masked men running from the scene but they have so far managed to elude NSW detectives investigating the case.
Hawi rose to prominence as the national president of the Comanchero and was involved in a brutal clash between his gang and Hells Angels members after disembarking a flight at Sydney Airport in 2009.
Bystanders watched in horror as the rival gang members punched and stabbed each other with scissors in the domestic passenger terminal.
Hawi was convicted and sentenced for the murder of Anthony "Tony" Zervas, 29, who was clubbed with a 17kg metal bollard and stabbed with a pair of scissors. He was jailed for a maximum of 28 years.
However, in 2014, the NSW Court of Criminal Appeal set aside the conviction and the following year Hawi was released from prison.
- additional reporting AAP
