Comanche - the pre-race favourite - flew a protest flag, accusing fellow supermaxi SHK Scallywag of tacking too close to her as the pair made their way out.
Scallywag, which completed a protest turn as a result, was forced to retire roughly six hours into the race after breaking her bow sprit.
Eleven of the race’s starting 103-strong fleet have pulled the pin, with some reporting damage and seasickness in challenging conditions which included a thunderstorm on the first night.
LawConnect navigator Chris Lewis described the stormy seas as “wild” with 180-degree wind shifts.
Moneypenny, URM Group and Alive are in a bunch about 90 nautical miles behind the two duelling leaders, with the third remaining supermaxi Wild Thing 100 further back in sixth.
URM Group has battled jib damage and lost her code zero spinnaker.
Shane Connelly, skipper of retired two-handed entrant Rum Rebellion, was briefly flung overboard on Boxing Day off the NSW coast in strong winds.
There may be further challenges for crews, with a strong wind warning in place on Thursday for waters off Tasmania’s east coast.