It will be his second runner in the Slipper – Single Gaze ran 10th behind Vancouver in the feature race three years ago.
This time he's hoping to crack the top five with Sunlight ($4.20 favourite) and Written By ($4.60) the two to beat in what Olive thought was a race with plenty of depth.
Olive pointed to the fact this year's edition of the Slipper had the highest cut-off in the race's history – the order of entry to get into the megarace is decided on prizemoney.
"Obviously I want to win, but if she finished in the top 20 I'd be happy, but more aiming for the top five," he said.
"I'd be ecstatic with a top five. Sunlight and Written By stand out, but I do think it's a very strong race and it's got a lot of depth."
He was a lot more bullish about Single Gaze's chances, with his stable star returning to the stage she ran on in 2015.
Like Sizzling Belle, she also finished second in the Black Opal before tackling the Slipper.
She's since gone on to win a group 1 race, as well as finishing second in last year's Caulfield Cup and running in the Melbourne Cup a couple of weeks later.
Gailo Chop ($2 favourite) was the only horse ahead of her in the market for the $700,000 Ranvet.
"I think she's in with a cracking chance. It's probably the softest race she's been in for a long time," Olive said.
"When I say softest it is group 1 so it's not soft, but compared to what she's been racing it's quite soft."
Barrier 1 can be far from ideal – a poor start means your horse will get swamped coming out of the barriers and get stuck on the fence at the mercy of the field.
But Olive felt his daughter of Sizzling had good enough "gate speed" to ensure she didn't get in early trouble.
His only concern was if there was lots of rain at Rosehill, which would turn the inside running into a quagmire.
On the other hand, a little bit of rain should suit his two-year-old filly.
Originally, Olive wasn't planning on running her in the Golden Slipper, but felt she did so well and was a "foolproof horse" so changed his mind.
The owners also wanted to have a crack at one of the biggest races in Australia – and he couldn't find a reason not to.
"It's obviously better than [barrier] 19. [Barrier] 1 can be a bit of a shitty draw, but the good thing with her is she's got gate speed so she can jump and put herself in a nice position," Olive said.
"That's an advantage. It's just if the track's wet, the fence is off, that's probably the only concern.
"She'll jump, put herself in a nice position from one and not have to cover too much ground."
Fellow Canberra trainer Matthew Dale will have his stable star Fell Swoop in the group 1 William Reid Stakes at Moonee Valley on Friday night.
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David Polkinghorne is a sports reporter at The Canberra Times.
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