The Branxholme horseman will start experienced campaigners Franco Santino and Triroyale Brigade alongside up and comer Pembrook Playboy and in the 2400m handicap.
The Wyndham Cup will be nothing new for experienced country cups campaigner Franco Santino, who starts from the back mark of 30m.
That handicap and the horse’s experience make the 5yr-old Williamson’s leading chance.
"I would probably lean towards Franco Santino. It’s a smaller field this week and don’t think the handicaps will be such a big problem," the trainer-driver said.
Franco Santino was off just a 10m handicap when ninth in last weekend’s Northern Southland Cup behind Henry Hubert.
Once the pacer got back on an electric closing 800m of 54.7sec he had no winning chance.
"I was pleased with him at Northern Southland. It was just one of those races he couldn’t get into," Williamson said.
"He usually begins pretty well, but he got squeezed up at the start.
"He hit the line strongly and I timed his last 800m in 54.5sec and last 400m in 26.5sec, so he couldn’t have gone much faster."
Pembrook Playboy comes into the race after producing a scintillating finish to beat older horses in his last start at Ascot Park.
Although the pacer clearly has the talent to match most of his rivals in tomorrow’s feature, Williamson is wary about what kind of position the horse will get into.
Pembrook Playboy will have just his second career standing start in the often tricky spot of barrier 1 on the 10m mark.
"Starting there is another reason why I would favour Franco Santino.
"He hasn’t had a lot of standing starts, so I am probably going to have to be a bit cautious with him early.
"He has had one stand and he paced away, but he was on the second row.
"I am confident he will pace away, but it’s just how much hustle and bustle there will be early to get him off the fence."
Leading driver Blair Orange will steer Franco Santino, with Williamson sticking with Pembrook Playboy.
Williamson’s knowledge of the pacer should help Pembrook Playboy begin as well as he can tomorrow.
Sticking with the 3yr-old will also allow the trainer-driver to keep a close eye on the horse’s progress towards next month’s New Zealand Derby.
"He is a lovely horse going forward and it wouldn’t surprise me if he come out and won.
"He has got the derby as a bit of a target in three weeks, so if I stay on him I will be able to assess his progress.
"I do think he is up to this race, but these country cup races can be the undoing of these young horses if they get too tough a run."
Tim Williams will drive Williamson’s third stringer, Triroyale Brigade.
The 5yr-old gelding steps back up a grade after convincingly beating a lesser line-up on Northern Southland Cup day.
"I can’t see a reason why he can’t go a good race again.
"He will step well and put himself in the race and if he is in the trail or three-deep he will be finding the line."
Lawrence (10m), Parama and Robyns Playboy (20m) look three of the biggest threats to the Williamson trio as they step back in class from last weekend’s Northern Southland Cup.
Lawrence battled into fourth after enjoying a perfect run behind Henry Hubert and Robyns Playboy ran sixth after getting off the speed.
Parama steps up in class after winning his last start at Wyndham.
