New Zealand's greatest jockey Lance O'Sullivan has made a triumphant return to Randwick with his first runner at the track as a trainer, winning the Group Two Chairman's Quality (2600m).

Sir Charles Road ($7) showed he was on target for the Sydney Cup on Saturday when he prevailed in a duel with Ventura Storm ($11) by a half-neck.

O'Sullivan, the son of champion trainer Dave O'Sullivan, retired in 2003, having ridden 2479 winners and now operates in partnership with Andrew Scott.

His Randwick wins included the ATC Oaks on La Souvronne in 1984 and Mr Tiz in the 1984 Galaxy.

"It's been a long time since I've been here," O'Sullivan said.

"He went well in the Auckland Cup so we thought we'd bring him over.

"He is the sort of horse who can back up so the week between runs to the Sydney Cup won't worry him.

"And Blake Shinn couldn't have ridden him any better."

Sir Charles Road, who races as Charles Road in New Zealand, finished sixth in the Auckland Cup (3200m), less than 1-1/2 lengths from the winner Ladies First.

"I guess you could call him a fast stayer," O'Sullivan said.

"He won't have any problem with the 3200 metres."

Shinn said Sir Charles Road got into a great rhythm.

"It was a marvellous staying performance. He relaxed lovely and I was able to get out at the right time," Shinn said.

"Once challenged he really dug deep and it was a really strong effort."

"It is great to ride a winner for Lance O'Sullivan and Andrew Scott and he's going to be a strong chance in the Sydney Cup."

The four-year-old is now on the third line of betting alongside Japanese horse Prestwick at $9 for the Sydney Cup behind Almandin at $3.50 and Aloft at $6.50.

Ventura Storm is in a group on $11 with senior Lindsay Park trainer David Hayes fined $200 for not telling stewards until just before the race the horse would be ridden more forward.

"I wasn't aware of the half-hour rule," Hayes said.

"But he went a lot better."