Trainer Ricardo Le Grange’s Leatherhead and Pennywise will race together for the fourth time in this Saturday’s $70,000 Class 3 race over the 1700m.

The pair has run against each other three times previously, all in Class 3 races over the Polytrack mile.

On January 2, Leatherhead wore down his stablemate late to hand the South African handler his first winner of the season in the form of a stable quinella.

The duo went separate ways after their last match-up on March 5. Pennywise was tested over 2000m for the first time about two weeks ago, while Leatherhead is back from a break and showed up in Tuesday's third trial, four days ahead of the highlight race on Saturday.

The Helmet six-year-old was paired up with Le Grange's highest-rated galloper Katak (102 points) in the 1000m hitout.

"This is part of his regular training because he pulls quite hard in his trackwork," said the South African handler.

"It was probably better to trial him in the week than getting him to go hard and have a gallop because it's much more controlled in a trial.

"He trialled really well. He's not out to set any record, but I was happy with the way he got to the line.

"He also cantered on Monday morning. He ran home a bit late at his last start (sixth).

"The extra 100m is no issue for him. Jake (Bayliss) will ride him this Saturday."

Bayliss was suitably impressed with the Paolo Mendoza-owned gelding after the trial.

"For a horse that runs in the 1700m, he is pretty sharp in that 1000m trial," said the Australian jockey who returns this weekend from a two-day suspension for careless riding.

"It's my first time riding him, and this trial would take the freshness out of him.

"I am confident. He will be a massive chance."

The five-time winner (all over the Polytrack mile) settled in second-last and had a quiet spin in the trial. He finished fourth, one length behind Kranji Mile contender Katak, and more than four lengths off the winner, trainer Alwin Tan's newcomer Griffin (Koh Teck Huat) .

Katak (Manoel Nunes) tracked the widest upon cornering, but steadily made ground in the straight to run third.

After his two Kranji wins came under the guidance of Australian jockey Danny Beasley, the latest at his last start in a Kranji Stakes A race (1600m) in February, the Cape Winter Series Triple Crown winner will be paired with leading jockey Nunes for the first time.

"He will have two trials before his first run in the Class 1 race over the 1400m on April 30, and then he will run in the Kranji Mile," said Le Grange.

"I just wanted him to have a nice and comfortable trial this time. Manoel was very happy with him. He will ride him at his next start.

"The horse is all good. We'll take it race by race for now, but beyond that, the (Singapore) Gold Cup is a possible target."

The $1 million Group 1 Kranji Mile (1600m) will be run on May 21 while the $1 million Group 1 Singapore Gold Cup (2000m), which used to be the third leg of the Singapore Triple Crown Series that included the Group 1 Raffles Cup (1600m) and the Group 1 Queen Elizabeth II Cup (1800m), will now be run as a standalone feature race on November 19.

Meanwhile, Pennywise gets back in trip and on his pet surface (all eight wins on the Polytrack). The six-year-old son of Pure Prize will have last-start partner Wong Chin Chuen back in the irons.

The 2019 Group 3 Colonial Chief Stakes winner ran fifth to Tangible in a 2000m race on turf at his last start, prompting Le Grange to conclude that staying races are not for him.

"We decided to try different things with him then. It was an okay run," said Le Grange.

"But I think I have come to the conclusion that he doesn't stay, and he's probably a far better horse on the Polytrack.

"We've brought him back to the 1700m on the Polytrack because he's obviously more comfortable in this.

"I'm happy with him. He galloped yesterday morning and he will wear the visors again in the races."

Raced by South African owner Bernard Kantor, Pennywise will carry 58kgs while Leatherhead will have 55kgs on his back. They will meet Trumpy, Tangible and On Line from the Michael Clements' yard, and last-start winner Strong N Best among others in the small field of eight on Saturday.