Sydney Cup winner Stand To Gain has snapped a long losing sequence as he enters a new phase of his racing career.

Stand To Gain, once a member of Chris Waller's all-conquering stable, had been winless since the 2011 Sydney Cup until he signalled he has a future over the jumps with an easy win in Wednesday's Caulfield Spring Dining On Sale Hurdle (3300m) at Sandown.

The seven-year-old was having just his second hurdle start and first for trainer Bob Challis after failing to finish as a short-priced favourite in his only other jumps appearance for Robert Smerdon last year.

The stayer had four unsuccessful flat runs after joining Challis's team but impressed connections in two hurdle trials.

He cruised along in front in the heavy conditions and, despite his untidiness over the final few hurdles, defied his $26 starting price to defeat Love Or Gold ($8.50) by 4-1/2 lengths with another 3-1/2 lengths to Fieldmaster ($4) third.

"I was a bit surprised with the trial form he had that he was that price," Liz Irwin, Challis's partner, said.

Stand To Gain's future will be in steeplechase racing with the plan for him to have one more hurdle start before stepping up to the bigger fences.

Irwin said they would take their time in asking Stand To Gain to contest the better jumps races.

"It's been a battle getting the horse in the right head space so we're not going to push him too hard," she said.

"By jumping standards he's still a young horse."

Earlier, the Patrick Payne-trained Chaparro scored a narrow win in his first steeplechase start of the season.

Chaparro, the $2.70 favourite, defeated Our Rockhampton ($3.30) by a half neck with 4-1/4 lengths to Makena Lei ($5.50) in third.