The last time bush jockey Ken Dunbar rode a Sydney winner was nearly 20 years ago.

As a 21-year-old, Dunbar steered the $41 outsider Gold Lease to a 2500m heavy-track victory at Canterbury in 1994.

And in a case of the stars possibly aligning for Dunbar, he is likely to encounter similarly wet conditions when he heads to Canterbury from Dubbo on Wednesday in an attempt to end a long run of city outs.

Dunbar's best chance will be aboard Sergeant Bilko, one of two horses he'll ride for Narromine trainer Lindsey Kennedy.

The city scene isn't new terrain for Dunbar, who at 15 started his apprenticeship in Melbourne with well-known trainer Rick-Hore Lacy.

He then moved to Albury before ending up at Rosehill with Barry Lockwood.

Dunbar, now 40, and his family moved to Dubbo 13 years ago to help a friend who had horses in work that needed riding.

It's a move that he has never once regretted despite few opportunities to return to ride at city meetings.

"I'll probably generally stick to out here - it's pretty hard to get a horse good enough to go to Sydney," he said.

"And then when you do get a horse good enough you've got to stay on it."

Dunbar knows Sergeant Bilko well, having ridden the five-year-old at his last six starts.

And he reckons he may be just the "tough sort of animal" who has a shot at some sort a city career - if he can race well in the Hyland Race Colours Handicap (1580m).

"Tomorrow will be the test to see what transpires and what he does," Dunbar said.

"He hasn't been far away in a fair few of the cup races out here and he bowls along fairly well, but we'll throw him in the deep end and see."

Dunbar will also ride Sergeant Bilko's travelling companion Lucky Cash in the Congrats @ Vinery Mdn Plate (1100m).