Celebrations for line honours winner LawConnect were muted early on Saturday morning, marred by the deaths during the fleet's first night of racing.
South Australian Nick Smith, 65, and 55-year-old West Australian Roy Quaden were killed in separate incidents as their vessels made their way down the NSW south coast.
Nick Smith died on Bowline after being struck by the boat's main sheet. (Paul Bramble/AAP PHOTOS)
Mr Smith, competing on Bowline in his fifth Sydney to Hobart, hit his head on a winch after being thrown across the yacht when he was struck by the boat's main sheet.
Mr Quaden was hit by the boom - the large horizontal pole at the bottom of the mainsail - while aboard Flying Fish Arctos.
Both crews, who subsequently retired from the event and limped back to shore, performed CPR on the men but were unable to save them.
Their bodies were returned to shore on Friday morning, and the boats involved have been seized.
Crew on board LawConnect tempered celebrations and held back on the usual champagne and trophy presentation in respect for the two men killed.
The Christian Beck-skippered supermaxi was first across the River Derwent finish line at 2.35am on Saturday in a time of one day 13 hours 35 minutes and 13 seconds.
Roy Quaden was fatally struck by the boom as Flying Fish Arctos sailed down the NSW coast. (AP PHOTO)
More than a quarter of the 104 yacht strong fleet that left Sydney Harbour has so far retired after an aggressive weather front, electrical issues and crew injuries prompted 29 boats to pull out by 11am on Saturday
Cruising Yacht Club of Australia vice commodore David Jacobs maintained conditions were not "excessive" and organisers would not be calling off the race.
But LawConnect crew member Tony Mutter described the conditions as the worst of his 11 Sydney to Hobart races.
While battling it out across the Bass Strait, Mr Mutter said the boat managed to escape sail damage, with his crewmates only picking up "bumps and bruises".
The crew of LawConnect tempered celebrations out of respect for two sailors who died in the race. (HANDOUT/ROLEX SYDNEY HOBART YACHT RACE)
"There was challenging conditions, probably the roughest race I've done out of the 11 that I've done .. but we came through okay, we didn't break too much stuff, and people are okay, just got a few bumps and bruises," he said.
The first night proved to be the toughest part of the race where his crew were "executing five gybes in 35 to 40 knots winds"
For crews remaining at sea, calmer waters lie ahead.
Navigator Adam Tillyer on Geoff Hill's Antipodes from Hong Kong described challenging conditions overnight ahead of clearer weather throughout the day.
"We're having a nice sail now," he said on Saturday.
"Last night we were in 35 knots, which wasn't on the forecast, so we dropped our gear down, because we were overpowered and it was tricky weather.
"We have a headfoil problem, so we've sewn hanks on the jibs, so we're a bit challenged, but in good shape though."
Vice Commodore David Jacobs said conditions had not been 'excessive' at the time of the fatalities. (Mick Tsikas/AAP PHOTOS)
Fellow navigator Clare Costanzo on David Griffith's Whisper said she expected to sail in by Saturday afternoon, with the crew looking forward to a cold beer.
"The race has been challenging - big waves across Bass Strait - not much sleep, but we keep pushing through those tough parts," she said.
Although LawConnect has claimed line honours victory for a second straight year, it may be days before the overall race winner is announced, after times are adjusted for handicap.
