Authorities allege the ring sold some 1.8 million bottles of wine over a four-year span, depriving the federal and provincial government of roughly $14 million in tax revenues.
Eleven people were arrested Tuesday by police in and around the Montreal area as well as in Ontario, including a presumed ringleader who is a wine specialist.
In addition, police say two others were part of the brain trust while others arrested were simply associated with the ring.
Two suspects remain on the lam.
The charges include fraud, conspiracy to commit fraud, trademark infringement and recycling the proceeds of crime.
Police said their investigation suggests only one type of wine was being imported from Italy and arriving by container in Ontario. It was then taken to First Nations Winery in Kahnawake, where it was allegedly rebottled with additives and flavours mixed in so it could be sold publicly under false names.
"The ring was offering about 20 types of wines, with counterfeit labelling and different flavours," said Cmdr. Marco Roy, head of a Montreal police squad that targets the underground economy.
Some 89,000 litres of wine have been seized since the investigation began in January 2014.