Bush trainer Mark Milton was left to wonder about the unpredictability of racing as he upstaged Sydney's biggest stable with a long-shot winner at Canterbury on Wednesday.

Still coming to terms with the loss of his best horse as a result of a fall which marred the Mudgee Cup, Milton trained Raised A Legend to win the All Too Hard @ Vinery Maiden Handicap.

In beating the Chris Waller-trained Elusive Star, Raised A Legend saluted as one of the outsiders in the 10-horse field as a $71 chance.

It was as welcome as it was unexpected, providing the Gulgong trainer with a change of fortune after Sooner Or Later had to be euthanased when he was one of five horses to come to grief in the Mudgee Cup.

"I guess some bad things turn around eventually," Milton said.

Sooner Or Later was a stable mainstay for Milton, winning five races as well as finishing runner-up in the Coonamble Cup, the Dubbo Cup and the Forbes Cup.

"He was a great little horse. He ran second in all those Cups but he couldn't crack one but he was knocking on the door all the time," Milton said.

Raised A Legend is Milton's second city winner and it comes more than four years after his first when Jali won at Warwick Farm.

The surprise result also gave apprentice Jake Pracey-Holmes a breakthrough at metropolitan level as he rode with a dash of daring usually reserved for a more senior rider.

Pracey-Holmes shot Raised A Legend to the front from an outside barrier before letting the three-year-old extend his advantage into the straight.

The three-year-old was set for a clear-cut win before Elusive Star ($4.80) made a late surge to get within a half head.

Milton said Raised A Legend was also entered for a country race on Friday but the decision to make the trip to the city was an easy one.

"He was in for Bathurst as well. I own him and the only person I've got to please is myself," Milton said.

"I thought I may as well get beaten here as getting beaten at Bathurst. So I said 'we'll come here and see how we go'.

"I was pushing that post back to get him home but I thought even if he runs second it's a pretty good effort."