Stirling Osland – Four Highway Wins In Brief Career

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Stirling Osland – Four Highway Wins In Brief Career

By John Curtis

STIRLING Osland was straight to the point.

“We don’t take a horse to Sydney unless we feel they have a serious chance of winning,” said Armidale’s leading trainer.

And the proof is in the pudding!

From only a handful or so of starters, Osland has already chalked up four TAB Highway victories and an important midweek success at Canterbury.

His Highway wins have been with Prada Miss (July 29, 2017), Radiant Choice (June 2, 2018), Point Counterpoint (November 20, 2021), and Golden Point (February 19 this year).

Prada Miss, Radiant Choice and Golden Point all won at Rosehill Gardens, whilst Point Counterpoint starred in the Highway at last year’s feature The Gong meeting at Kembla Grange.

The same horse also gave him his “first actual Sydney winner”, to use his own description, when he took a Benchmark 72 Handicap (1550m) at Canterbury on September 21 after snaring the Moree Cup (1400m) at Tamworth 17 days earlier.

That was the gelding’s first start since finishing runner-up to Beckford in his hometown Armidale Cup (1600m), which was also run at Tamworth last December.

One of country racing’s brilliant young trainers – he turns 33 years of age this month – Osland understandably derived special pleasure from his initial Sydney success with Prada Miss five years ago.

Armidale trainer Stirling Osland. Photo: Bradley Photographer.


“I broke her in, and she went to Chris Waller initially,” Osland explained.

“She had a few trials for him, but didn’t race and came back to me.

“We won a 3YO Maiden (1100m) with her on debut at Armidale in December, 2016.

“Prada Miss had been runner-up in both a 1600m Listed race for three-year-old fillies at Doomben and the Mother’s Gift (1400m) at the Grafton July carnival before winning the Highway at Rosehill, with Hugh Bowman aboard.

“She was only my second ever starter in Sydney, so it was a great thrill to win that race with her.

“Prada Miss won four races before we sold her as a broodmare in 2018 for $190,000 to Queensland interests. She was a good mare to us.”

It was surely no coincidence that Ben Looker was Prada Miss’ jockey when she made a winning debut for her trainer at the Armidale meeting nearly six years ago.

He rode her in two of those four wins and, with 33 victories, has clearly been Osland’s most successful jockey.

Born at Tamworth, Osland has always been around horses, though not initially thoroughbreds.

“Though I didn’t come from a racing family, we always had polo ponies and campdrafters,” he said.

“I went to school at Armidale and college in Melbourne, and then travelled around for five or six years, working on stations in the Northern Territory and breaking in horses at the former Eliza Park Stud (now Sun Stud) in Victoria.”

Osland returned home to work for Gerry Harvey at his Broombee Stud near Armidale – a move which eventually led to him taking the bit between his teeth and launching his training career.

“I broke in horses for three or four years and leased some stables in town at Armidale racecourse,” he said.

“When I got sick of chasing horses to break in and had a couple of pre-trainers, I felt the time was right to take out my licence at the beginning of the 2014-15 season.”

Osland’s inaugural runner was Harlequin’s Gold, who finished a distant ninth in a field of 11, after showing pace, in a Benchmark 55 Handicap (1200m) at Tamworth on September 2, 2014.

He was ridden by then 4kg claimer Melinda Turner (now a Sky Racing analyst) and had only one more run when fourth at the Come-By-Chance picnic meeting 18 days later before being retired.

It was tough going in the early days with only a couple of horses, but Osland got that often elusive breakthrough winner out of the way when New Endeavour (Matt Paget) beat nine rivals in a 2YO Maiden Plate (1000m) at Gunnedah on January 12, 2015.

The Casino Prince gelding had only three runs for Osland before being prepared by a number of trainers (Leon Corstens in Melbourne and Chris Waller and Jason Coyle in Sydney) before returning to his Armidale base.

Osland won another seven races with the overall 10-times winner, who was retired last year and remains in his care.

He says he owes much to both New Endeavour and another of his early horses, the now deceased Rage Against, with whom he also won eight races (including a 2100m Benchmark 62 Handicap at Wyong and 1900m and 2050m Spring Cups respectively at Armidale and Gunnedah).

Osland keeps on average 20-24 horses in work at Armidale, where he can work his team daily on the inside sand track along with the course proper each Tuesday morning.

“I have been as low as 18 and up to 28, and will be able to accommodate more if Armidale Jockey Club’s plan to build another eight boxes with yards becomes reality in the near future,” he said.

Since beginning his career in 2014-15 and winning two races that season, Osland has showed both his skill and mettle by topping double-figures with winners each subsequent season.

His latest success with four-year-old Pierro mare Special Day at Tamworth on October 6 was the 134th time he has visited the winner’s stall.

“I’m very fortunate to have the support of prominent breeder-owners such as Matthew Sandblom and Stuart Ramsey,” Osland said.

“Matthew owns Point Counterpoint and Golden Point, and Stuart’s Special Day was having her first start for me when she won at Tamworth.

“I have been enjoying a terrific run with his horses, winning five or six from the last eight I have started for him.”

Osland had hoped to celebrate his first ever starter in The Kosciuszko (for country trainers and now carrying a $2m prize tag) with Golden Point at Royal Randwick last Saturday, but unfortunately the gelding sustained a serious injury in what was to have been his final lead-up, at Hawkesbury on September 22.

The Bull Point five-year-old had impressively won the Tamworth Rush (1200m) first-up on August 29 and started favorite in a 1300m Open Handicap, but tailed the field of five home.

Subsequently, it was discovered the gelding had fractured his pelvis.

“I don’t know how it happened, but Golden Point stayed at Hawkesbury for several weeks afterwards,” Osland said.

“He will have a lengthy spell recuperating at his owner’s property, and time will help him heal.

“Obviously, it would have been a great experience to have a runner in The Kosciuszko, but all going well I expect to get him back to the stable in May or June next year.”

Osland had planned to head back to Sydney to run his recent Canterbury winner Point Counterpoint in the Big Dance Wild Card at Randwick last Saturday, but there was further disappointing news.

Unfortunately, he had to scratch the gelding because of filling in a fetlock.

The first and second placegetters automatically won exemption from ballot for the inaugural $2m The Big Dance (1600m) at Randwick on Melbourne Cup day (November 1).

“It’s a six to six and a half hour trip to Sydney, and we go the day before the meeting and stay overnight,” Osland said.

“I don’t go to town too often, and definitely not unless I consider I have a genuine winning chance.

“I’m sure my record in Sydney shows that.”

Osland and his wife Courtney have a six-months old daughter Heidi and live on their 100-acre property about seven kilometres from Armidale racecourse.

“It’s a nice set-up with seven five-acre paddocks, and it’s not far to town each morning,” he said.

“We have started a young family, and are happy with what we’re doing. There’s no need to consider moving closer to Sydney or the provincial tracks.”

. HOOFNOTE: Osland has twice trained 26 winners in a season, the first in 2017-18 and again in the season just concluded.

“My goal is to keep improving, and increase the amount of winners I train each season,” he said.

“I had an ordinary year in 2019-20 (10 winners) when the drought severely impacted training because of water restrictions and very firm tracks, but picked up again with 17 the following year and then 26 last season.

“I have already had seven winners since the new season began in August, and am confident I can better that figure.”

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