And on Sunday, the Scone-based trainer managed to do so, with Fingers Hunter winning the $200,000 feature at the Wellington Race Club.

A happy hunting ground for some, Cavanough said he was confident heading into the meeting but was more relieved for his apprentice jockey, Braith Nock.

"Absolutely, (I'm pleased)," he said of the win.

"There is a carnival in QLD and a fillies race at Scone, but even more importantly, my apprentice, Braith, has had 19 or 20 rides here and hasn't had a winner.

"He missed a lap here one day and got a couple of months suspension, so it was just a great buzz.

"When you come to Wellington, you want to win the Boot and we got it."

The two-year-old stormed home down the straight to just hold on for the victory over the 1100m race in front of a strong Wellington crowd.

In one of the biggest races outside of Sydney for two-year-old horses, Cavanough couldn't help have faith in Fingers Hunter ($8.50) who had just started once before Sunday.

"I was very, very confident coming to the races, she'd been working really well at home," he said.

"Her first up start was brilliant under the circumstances and she ran super, then we just said we'd go to the Boot with her and everything just fell into place."

Damien Lane's Sneaky Sofia ($21) finished second more than a length ahead of his other runner Canamble ($3.70).

Elsewhere, Michael Gatty and Olivia Chambers combined for two race wins at Wellington.

Chambers rode Peruno in the Western Truck Group Country Magic Class 1 Showcase Handicap (1100m) for the photo-finish win.

The duo then repeated their form later in the day with Gorush Lightning ($61) shocking many to win the KFC Zinger Stacker Benchmark 66 Showcase Handicap (900m).