The heydays of entrants, Filepro, Ultimate Challenge and Lawless go back many years but these evergreen ocean racers are still ranked as good prospects in this year’s exceptionally high-quality fleet.

The L2H will start from Beauty Point at 9am on December 27 for the 285-nautical-mile dash down Tasmania’s rugged north-east and east coasts.

The early start is to give yachts the least problems with tide in the short dash to Low Head and Bass Strait.

Filepro, a David Lyons-designed 40-footer, originally named Micropay Cuckoo’s Nest, won the 1993 Sydney-Hobart on corrected time after surviving a gale-force battering in the Tasman Sea.

Since then the yacht has had a number of owners and names, and sailed in various states. A syndicate of Bellerive Yacht Club members bought her in 2016, renaming her Filepro.

Skipper of Filepro for her first L2H race is Tim Gadsby with the yacht’s most recent success being an overall PHS handicap win in the Maria Island Race.

Ultimate Challenge, a Dubois 40, sailed to fame in winning the 1989 Sydney-Hobart and as a member of the Australian team at the Admiral’s Cup under the ownership of the late Lou Abrahams.

Hobart yachtsman Peter Jenkins acquired the ageing ex-one tonner a few seasons ago and has added a rather whimsical assessment of the near 30-year-old boat and her crew.

“Their trophy cabinet is full of empty beer cans, broken boat bits and random pairs of sunglasses,” he said.

“In the unlikely event this crew stand on top of a podium they will sure have a party like no other!”

Despite the crew’s pessimistic assessment of their prospects, the Derwent Sailing Squadron-based Ultimate Challenge finished third in PHS in last year’s race and has been in the top of handicap results in Hobart this summer.

Lawless, a Green 31, was designed by Victorian John Green and skippered by him in the 1984 Sydney-Hobart, finishing second overall.

Prominent Port Dalrymple Yacht Club member Stephen McElwee now owns the veteran, but still competitive sloop which will be sailing in her fifth L2H.

Lawless won the PHS category of the 2015 L2H and could be one of the leading Northern entries.