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Supermaxi Black Jack has overcome a rocky preparation and rugged seas to take out line honours with the slowest Sydney to Hobart victory time in 17 years.

The Monaco-registered 100-footer crossed the River Derwent finish line in darkness at 1:37am (AEDT) on Wednesday.

Its time of two days, 12 hours, 37 minutes and 17 seconds was the slowest since Nicorette III's win in 2004.

Black Jack had been locked in a tight three-way tussle down Tasmania's east coast with LawConnect, which finished second trailing by about two-and-a-half hours, and third-placed SHK Scallywag 100.

This year's fleet was decimated by rough seas on Sunday and Monday, with 36 of the 88-strong starting field forced to retire.

"It was tough in the beginning. The first 30 hours were pretty rugged," Black Jack skipper Mark Bradford said.

"We had a tough race with both the other (supermaxis). We dropped Scallywag at the end for a bit but she came back and LawConnect was right there the whole way."

Black Jack previously claimed line honours in the 628 nautical mile bluewater classic in 2009 under the name Alfa Romeo.

It finished fifth in the most recent Sydney to Hobart in 2019 and was second to Wild Oats XI by just 28 minutes in a 2018 thriller.

Owner Peter Harburg for the first time did not race with Black Jack but was at Constitution Dock in Hobart to greet his team after riding them home.

"It is very emotional. It is the grand prize of yachting in Australia. For me it's the first time I've been involved in a winning team," he said.

"I don't know whether I want to cry or laugh or give Mark another hug. I can't describe it."

Black Jack missed a chance to compete against LawConnect and SHK Scallywag 100 in the inaugural Australian maxi championship earlier this month because a crew member tested positive for COVID-19.

Their program had already suffered a setback when the boat's mast broke in the Brisbane-Gladstone race in April.

"We started with a 66-footer as Black Jack and we've worked up to this," Harburg said.

"We've won every race on the east coast of Australia and we've beaten every other yacht on the east coast of Australia at different times.

"But this is the prize that has eluded us all along."

Bradford said Black Jack only suffered minor breakages in a race where many smaller competitors have reported hull damage and other serious issues.

© AAP 2021

Duelling Sydney to Hobart supermaxis Black Jack, LawConnect and SHK Scallywag 100 could be set for a line-honours battle up the River Derwent.

Monaco's Black Jack held an 11 nautical mile lead at 7.30pm (AEDT) on Tuesday after a day-time tussle with LawConnect down Tasmania's east coast.

LawConnect, a previous winner as Perpetual LOYAL in 2016 and Investec LOYAL in 2011, was second for most of the day but was neck-and-neck with Hong Kong's SHK Scallywag 100 in the evening.

The 100-footers capitalised on strong breezes but will likely have to deal with typically still conditions when they hit Hobart's River Derwent.

Cruising Yacht Club of Australia commodore Noel Cornish said a finish about 2am on Wednesday was expected.

"There is a chance they could be match-racing up the Derwent after two solid days of racing," he said.

"Black Jack is lighter and would go better in lighter conditions. LawConnect is a better boat, wider in the heavier conditions. How that plays out in reality, I don't know.

"Often the Derwent does shut down on breeze ... it often happens around 10pm."

The tightest finish in race history came when Condor of Bermuda pipped Apollo III by seven seconds in 1981.

LawConnect has experienced problems with its position tracker, with its location instead determined through radio reports.

This year's 628-nautical mile event is one of the slower in recent years, a long way behind Comanche's 2017 record of one day, nine hours, 15 minutes and 24 seconds.

Black Jack navigator Alex Nolan said the crew was "pushing hard" in lighter conditions on Tuesday morning.

Once they arrive in Hobart, all crew will need to complete rapid antigen COVID-19 tests before they're allowed to disembark.

Any positive tests will require the whole crew to quarantine while the positive person undertakes a PCR test.

Rough seas on Sunday and Monday wiped out more than a third of the fleet, with 36 of 88 starting yachts forced to pull the pin.

Rouge Wave, a NSW entrant in the new two-handed category, became the latest to retire on Tuesday after reporting unspecified damage.

Adrienne Cahalan, who has contested 29 Sydney to Hobart events and is the most-capped female sailor, is back in the pack as navigator aboard Oroton Drumfire.

"It's going to be a really big achievement to finish this race because we've had such a variety of conditions so far," she said.

Quest, Celestial and Ichi Ban are among the handicap frontrunners.

Tasmanian boat Sidewinder is leading the new two-handed category, boats sailed by just two people, ahead of nine remaining competitors.

Two-handed entry Maverick was forced to retire on Monday night after hitting "something heavy".

Co-skipper Rod Smallman said the boat's rudder was damaged and part of the deck was shattered.

"We were taking a bit of water but there was not a safety issue," he said.

© AAP 2021

Duelling Sydney to Hobart supermaxis Black Jack and LawConnect could be set for a line-honours battle up the River Derwent.

The pair were neck-and-neck down Tasmania's east coast on Tuesday, followed closely by Hong Kong's SHK Scallyway 100 which is considered an outside chance.

Monaco's Black Jack held a seven nautical mile lead at 5pm (AEDT), with LawConnect, a previous winner as Perpetual Loyal in 2016 and Investec Loyal in 2011, in second.

The 100-footers capitalised on strong breezes but will likely have to deal with typically still conditions when they hit Hobart's River Derwent.

Cruising Yacht Club of Australia commodore Noel Cornish said a finish about 2am on Wednesday was expected.

"There is a chance they could be match-racing up the Derwent after two solid days of racing," he said, not ruling out a charge from SHK Scallyway 100.

"Black Jack is lighter and would go better in lighter conditions. LawConnect is a better boat, wider, in the heavier conditions. How that plays out in reality, I don't know.

"Often the Derwent does shut down on breeze ... it often happens around 10pm."

The tightest finish in race history came when Condor of Bermuda pipped Apollo III by seven seconds in 1981.

LawConnect has experienced problems with its position tracker, with its location instead determined through radio reports.

This year's 628-nautical mile event is one of the slower in recent years, a long way behind Comanche's 2017 record of one day, nine hours, 15 minutes and 24 seconds.

Black Jack navigator Alex Nolan said the crew was "pushing hard" in lighter conditions on Tuesday morning.

Rough seas across the first two days have wiped out more than a third of the fleet, with 36 of 88 starting yachts forced to pull the pin.

Rouge Wave, a NSW entrant in the new two-handed category, became the latest to retire on Tuesday after reporting unspecified damage.

Adrienne Cahalan, who has contested 29 Sydney to Hobart events and is the most-capped female sailor, is back in the pack as navigator aboard Oroton Drumfire.

"It's going to be a really big achievement to finish this race, because we've had such a variety of conditions so far," she said.

Quest, Whisper and LCE Old School Racing, all from NSW, are among the handicap frontrunners.

Tasmanian boat Sidewinder is leading the new two-handed category, boats sailed by just two people, ahead of nine remaining competitors.

Two-handed entry Maverick was forced to retire on Monday night after hitting "something heavy".

Co-skipper Rod Smallman said the boat's rudder was damaged and part of the deck was shattered.

"We were taking a bit of water, but there was not a safety issue," he said.

© AAP 2021