It took until start No.57 for Pretty Possum to break her city duck with connections hoping it won't be as long for her second success.
On Saturday the mare runs at Flemington in the Jockey Celebration Day Handicap over 1000m after winning at Moonee Valley on July 13.
Pretty Possum is also the winner of nine races on bush tracks and Osborne is surprised she is at $31 with Gun Case, who ran a similar time at Moonee Valley, the $4.80 favourite.
"I don't think she'll be too far away if everything goes well," Osborne said.
The trainer, who is also the mare's co-owner, plans to race Pretty Possum for another year, saying she rarely puts in a poor performance.
He has the 955m races at Moonee Valley in mind when night racing resumes.
"If she put in a couple of bad ones she might go to the barn this year," Osborne said.
"But in the breeding season we like to go down to Moonee Valley for those night meetings.
"It's a bit of break and a fun sort of night for everyone, so she'll probably do this season and go to stud next year."
Two races after Pretty Possum lines up, Osborne will be watching Just Stellar, a horse he swapped for a Jack Russell pup.
Trained by Chris Davis, Just Stellar failed narrowly at Flemington at her last start on July 23 over the 1400m of Saturday's VRC Member John Lee Handicap.