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Trainer Stephen Gray reached a major milestone in his Singapore training career when Pusaka gave him his 500th winner on Sunday.

The New Zealander, who relocated from his Waverley training base in the Central Districts to Kranji in 2000, has known his ups and downs before he achieved that significant target, but took great pride he has stayed the distance.

Looking back on his Singapore stint, Gray cannot complain with the mark he has made on the local racing scene, given the less impressive arsenal at his disposal compared to the big guns like Laurie Laxon or Michael Freedman. He is above all happy he keeps his owners happy.

Toasting to his landmark win at the winner’s circle, Gray was understandably a touch emotional as he reminisced about his successful journey in a land he once only knew as the remote country where his trainer-father Kevin sent horses to some wealthy Asian clients.

“When I first came here, I was 35, young and hungry. I’ve worked hard and stuck it out throughout those last 14 years,” said Gray.

“The place has changed remarkably. I’ve seen a lot of changes and I’ve grown with the place, with the Club, which to me has the best racing model in the world, though I understand there are some restrictions.

“I myself have grown a lot, mentally and maybe physically (while he pats his tummy), but it’s all been mostly change for the better. I got married to Bridget when I was here and our two kids, James and Katie were born here.

“It’s a pity Bridget could not be here today to celebrate my 500th winner as she has to be with the kids who are riding at a show jumping event.

“But one thing I take great pride in is there are only four trainers left from the time I started out in 2000, Laurie Laxon, Michael Clements, Mohd Yusof and myself. That to me is a feat on its own.”

Gray said he and Bridget had a treasure chest full of good memories as they look back from the top of his haul of half-a-tonne, namely big race wins like the Emirates Singapore Derby with Lim’s Prestige in 2007, Given Vision who gave him two Legs of the Singapore Three-Year-Old Challenge or the recent ascent of Emperor Max in the Kranji sprinting ranks, but like in any rollercoaster ride, there were also low points.

“Last year was one of my worst years. The stable did not do too well, but the death of WX (Wei Xiang) Wong affected me the most,” said Gray of his former apprentice jockey who died in a trackwork accident in January 2014.

“It took a long time to recover as he was like part of the family and he had the whole future in front of him. But we had to move on, for him, for the owners, for ourselves.”

Gray said he would love to still be around for the next big milestone – 1,000th winner, and though he will probably carry on with an unchanged philosophy, he foresees a rough ride ahead.

“The next two years or so will be tough. There are challenging times ahead,” he said.

“But that’s what we do for a living. I’m lucky to have very good staff, Bridget, Peter Hutton and all the boys behind me and you can count on us to be around to take these challenges head-on in the years to come.

“I sure would love to train my 1,000th winner one day. If Laurie did it, why not me, as I’m still young.”

The likes of Pusaka or his 499th winner Bhaskara on Friday and their owners, new Indonesian outfit Dago Stable, are among those who represent Gray’s new driving force as he moves forth.

“It’s great that (owner) Untung (Joesoef) has won another race with another “repossessed” horse,” said Gray referring to how both Bhaskara and Pusaka became “bad debts” after the original buyer bailed out.

“I thought Pusaka had a chance today and when my other horse Holding Fast fought out the finish with him, I knew I couldn’t lose.”

Well ridden by Michael Rodd (pictured above with Gray), Pusaka (x Dane Shadow) looked home and hosed when he came with a strong run on the outside, but stablemate and $108 longshot Holding Fast (Rueven Ravindra) poked up on his nearside to issue a stiff challenge. Either way, Gray had his 500th winner, who was in the end decided by a head between his stable 1-2 on the photo print.

Even-money favourite Falcon (Manoel Nunes) had every chance when he emerged at the 300m, but was outsprinted by Gray’s pair to settle for third another length away. The winning time for the 1400m on the Short Course of the $35,000 Maiden Division 2 race was 1min 23.74secs.

Though Rodd is only a newcomer at Kranji compared to a "veteran" like Gray, the Australian jockey was quickly earning his stripes on the local circuit when he went on to ride a double aboard Mala Mala in the $35,000 Maiden Division 1 race over 1400m. The Melbourne Cup-winning jockey is licensed for only three months, but now looks a shoo-in for an extension given he has already booted home nine winners in only 53 rides.