Both gallopers have put prior below-par runs behind them with excellent last-start performances before the 1600m feature.
Rosewood comes into the $100,000 event after chasing home rising Central Districts star Helena Baby in the Opunake Cup.
Trainer Marilyn Paewai said she was rapt with her horse's performance.
"We were pretty pleased with that run.
"That was a quite special run from her [Helena Baby], I thought."
Her runner-up effort put Rosewood's prior failure in the Tauranga Classic behind her.
Paewai put that failure during Rosewood's otherwise brilliant winter down to the horse not handling racing right-handed.
With the 5yr-old's preparation back on track and having barrier 2 and the services of Lisa Allpress, the timing appears to be perfect as Rosewood seeks an elusive group race victory.
"She has galloped OK [yesterday] and she has settled in well down at Riccarton so everything seems to be all right with her.
"The ground is pretty wet and it would be nice if she could get that group win."
The Opunake Cup clearly looks the most essential form race for punters to analyse.
Winter Cup contenders Herengawe (third), Red Sierra (fourth) and Platinum Rapper (seventh) chased Helena Baby and Rosewood home in the race.
Herengawe and Red Sierra and fellow Central Districts raider Dez have been rated the $7.50 equal second favourites behind Rosewood in betting this week.
The connections of Dez have done well to secure the services of leading South Island rider Chris Johnson.
He immediately turned around an up-and-down winter for Dez when the pair combined for a win at Otaki last weekend.
"I was fortunate enough to get Chris to ride him in a jumpout and then I was lucky enough to get him for Otaki and it has worked well," trainer Simon Wilson said.
Dez's below-par efforts in the three prior starts of his preparation were put down to the horse being in unsuitable races.
"I have just made a few bad decisions with which races I have chosen with him this preparation.
"He ran well and he seems to have come through the race well."
Johnson rode both Herengawe and another Central Districts contender, King Cougar, in their most recent starts.
King Cougar went agonisingly close to winning the rescheduled Oamaru Cup when nosed out by Trudeau.
Trudeau and topweight Who Dares Wins give trainers Tony and Lyn Prendergast a strong hand in the Winter Cup.
Trudeau, who has a massive 7kg advantage over his 60kg top-weighted stablemate, has progressed well since winning last month's Oamaru Cup.
"He's come through the win really well and we're pleased with him. He's a lightweight chance," Tony Prendergast told NZ Racing Desk.
Who Dares Wins began his campaign in brilliant style with a hat-trick of wins, before failing in his most recent start in the Amberley Cup.
The 7yr-old had progressed well since that run and was ready to put it behind him on Saturday, Prendergast said.
"He was just a wee bit over the top at his last start.
"He wasn't quite 100% but he's picked up a lot since then. He's had a break and he's come back really well, so we're happy with him."
Who Dares Wins is rated the second equal favourite among the South Island chances in the Winter Cup alongside Albut Me at $18.
Last-start Trentham winner Flying Sardine heads the southern contingent at $11.
