Andoo Comanche and LawConnect are within sight of each other as they enter the Derwent River after flying around Tasman Island just after 4am (AEDT).

Andoo Comanche narrowly led over LawConnect as the two yachts went past Port Arthur and the fight will go right down to the wire as they navigate the Derwent.

As of 6am, there was just 300m separating the pair as far as distance to go.

It may be a problem on the opening night of sailing that ends up costing LawConnect a famous win.

LawConnect’s Tony Mutter described the drama on the first night when his yacht lost a main sail in the wild weather, News Corp first reported.

“The first day went okay through the daylight hours, and when night time came all hell broke loose because there was plenty on,” he said.

There have now been 11 retirements from the fleet of 103 yachts — but there are fears the number will grow dramatically on Thursday when the conditions are set to take a turn for the worse across Bass Straight.

The problems are with the rest of the fleet, with only a handful of boats having actually cleared Bass Strait so far.

“There could easily be 30 retirements by tomorrow night,’’ meteorologist Roger Badham told News Corp late on Wednesday.

“There’s far worse to come for them. It’s not a nice place to be, Bass Strait tomorrow (Thursday). It just gets increasingly bad all day.’’

Scallywag was the first big casualty of the race after the Hong Kong-based sailing team’s bow sprit — which carries the yachts biggest sails — broke just hours into the race.

Scallywag had been the early leader and was in a fight with Andoo Comanche and LawConnect before it was forced to abandon its campaign.

Two more vessels were forced to retire in the early hours of Wednesday morning with Sticky and Maritimo 52 pulling out.

Sticky was forced to pull out with electrical damage, while Maritimo 52 had damage to rigging.

Small yacht Rum Rebellion was hit by a burst of water between Cronulla and Wollongong sending the boat on its side.

Shane Connelly was taken overboard and was a few metres from the boat but was able to swim back to it.

“We are both well and the main thing is our systems and drills all worked well,’’ he told News Corp.

As first reported by News Corp, Arcadia on Tuesday returned to Sydney with a torn mainsail and Rum Rebellion also turned back due to an unspecified reason.

Reigning champions Andoo Comanche and LawConnect are continuing to battle for line honours as they head towards Bass Straight.

Tuesday’s retirement was a gut-punch for the Scallywag crew which had already declared the 2023 Sydney to Hobart would be its last.

News Corp reported skipper David Witt and his crew were “devastated”. The vessel has returned safely back to Sydney.

The team earlier confirmed their sad news via its social media channels.

RETIREMENTS IN THE 2023 SYDNEY TO HOBART

Arcadia – Retired – mainsail damage

Currawong (TH) – Retired – electrical issues

Maritimo 52 – Retired – rigging damage

Pacman (TH) – Retired – runner damage

Rum Rebellion (TH) – Retired – minor injury

SHK Scallywag – Retired – broken bowsprit

Sticky – Retired – electrical damage

Georgia Express – rigging issues

Millennium Falcon – Retired – crew illness

Tumbleweed (TH) – Retired – crew illness

Luna Blue – Retired – damaged equipment