Taree trainer Ross Stitt is hoping for a repeat of Single Spirit's only other visit to Kempsey when the five-year-old contests the Wauchope Cup.
The nine-time winner's only other trip to the Mid North Coast track was in May 2013 when he won a Class Three Handicap over 1450 metres, the same distance as Sunday's $27,000 Cup.
He carried top weight of 59kg that day and jumped from barrier 11.
On Sunday Single Spirit faces a similar task under 60.5kg and barrier 15.
"He's got it all against him with top weight and the outside draw," Stitt said.
"But I guess he's got Robert Thompson aboard and that can mean a lot."
Recently inducted into the Australian Racing Hall of Fame, Thompson was also awarded a Medal of the Order of Australia in this week's Queen's Birthday honours list.
Thompson has ridden more winners than any other Australian jockey and has had an association with Stitt of more than 20 years.
It will be the first time Thompson has ridden Single Spirit in a race since they combined for third in last year's Wauchope Cup run at Port Macquarie.
Stitt will leave it up to his friend to negotiate a path from his barrier but does not expect him to be in front.
"It's never good out there," Stitt said.
"It will be up to him (Thompson). I just hope he can get in there somewhere and have some luck. He'll need it."
Single Spirit has led in his past two starts when unplaced in the Gunnedah and Wingham Cups but Stitt that would not be the case on Sunday.
Stitt said Single Spirit had a niggling leg problem which required careful management but was fit and well.