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William Freedman wants to see the Rosehill surface improve before starting A Shin Rook in the Winter Challenge.

William Freedman will need to see the Rosehill surface dry out before he saddles up A Shin Rook on Saturday.

The Japanese-bred gelding is nominated to tackle the Listed Winter Challenge over 1500m in just his second start for Freedman.

The seven-year-old has performed well first-up in the past but had a setback after finishing last in the Group 3 Festival Stakes in November.

Freedman says if the track continues to dry out, A Shin Rook will be sent around on Saturday.

"If the track keeps drying out, I think they had it up a Soft 7 today (Monday), he'll go around," he said.

"He's got good first-up form, but he's a bit older now and he might need a run for fitness.

"It's a small field, I'm not sure it's a weak field, but it's a smaller field, it might give him a chance to settle a little bit closer than he normally does.

"Country trials can sometimes be a little misleading, but if he turns up with the first-up form that he's produced before, then he could run a race.

"He'll be long odds, but you can always hope."

A winner of six races, A Shin Rook has only been in Freedman's care since the middle of last year.

He ran first-up in the Festival Stakes at Group 3 level, but was then sent to the paddock again, with the rising eight-year-old sent for tie-back surgery.

He has since trialled at Scone, and Freedman says the son of Heart's Cry will be targeted toward country features if he can produce a good run at Rosehill.

"He's come back from a throat operation, he had tie-back surgery after his last start," he said.

"I actually think, being a bit later in his career, he's probably going to be looking for a little bit further than he previously has run.

"I'm hoping that if he runs well on Saturday, we might target a race like a Coffs Harbour cup, something like that.

"Something like the quality country cups out this way, I think that might be his go.

"He's had his fair share of issues, but his heart still seems to be in it, he still wants to be a racehorse."

Freedman will also have a runner in the Highway (1500m) with Birdonawinningpost making another trip to Sydney.

The rising five-year-old was beaten 5.5 lengths in her first-up assignment at Randwick two weeks ago.

Freedman says the first-up run wasn't a surprise, with the real target being another Highway in a fortnight's time.

"She is going well. Her first-up run was no surprise to me, she just knocked up," he said.

"We've tried to get her ready for the 1800m Highway which is two weeks after.

"But it's quite a good progression to go from 1400m to 1500m and then she'll go to 1800m.

"She'll run a much better race this time, she might find one a little bit fitter than her that wins over 1500m.

"But if you look out for her in a fortnights time, she'll be pretty hard to beat."