Sent out a $5.50 chance in a market dominated by the Gai Waterhouse and Adrian Bott-trained Northern Voyage, the New Zealander cruised to victory in the hands of Thomas Sadler, whose 3kg claim looked an unfair advantage.
"We always thought he would be competitive in Australia and I think he has improved a little bit from last year. He has got a little bit stronger," Gillies said from Warrnambool on Saturday.
"We were stoked with the win yesterday and Tommy was rapt. He rode him at the trials the week before and he just had a look around because he hadn't schooled since last year and the fences here are a bit different. The hurdles are a different colour and they don't have the soft padding on the front and they're a little bit smaller.
"That brought him on and he was a lot more switched on and fitter yesterday."
The honest flat performer, turned jumper has taken to his new vocation with aplomb.
Having just his third start over hurdles, Woodsman has two victories to his name and a runner-up finish in last year's Hawke's Bay Hurdles (3100m) won by quality veteran No Change.
"He does have a high cruising speed and he jumps fast and lands on the other side running," Gillies said.
"The track suited him down to the ground yesterday, as he struggles to handle heavy ground and that is why we gave him only the two hurdle starts in New Zealand last year and targeted Australia this season."
It was the first Australian start for the Mastercraftsman gelding, who will now head towards the A$150,000 Galleywood Hurdle (3200m) at Warrnambool on May 6, but a flat outing in between looks on the cards.
"If they keep racing, he will have a run in the Terang Cup (2150m) as a lead-up to the Galleywood," Gillies said.
Gillies and wife Pam have been staying with Warrnambool trainer Patrick Ryan.
"We leave today to get to Melbourne and we fly home on Monday," Gillies said. "There is one flight and then none for a week, so we decided to come home and if racing continues here Patrick will look after the horse and train him.
"He has stables right on the course, which has been ideal for him and he has a farm out of town and Woody is going out there today for a few days.
"Karen Fursdon put us in touch with Patrick and he was only too happy for us to come over. He is a champion bloke and has been very accommodating."
Gillies, who also works for Te Akau Racing in the mornings, said Woodsman was the only horse he had in training.
"That's why we thought we would go over and have a bit of a working holiday with our horse," he said.
"That has been knocked on the head but we were stoked just to have the opportunity to race yesterday.
"If they do shut down here, he is in the right place because when New Zealand is back racing we will probably have wet tracks again, whereas they might run some of the jumping features later in the year here."
The winner of 8 races on the flat, with a further 9 placings, Woodsman is raced by the Gillies in conjunction with long-time owner Ron Thompson.
"He was my first ever client when I started training," Gillies said. "I have had horses on and off for him for the best part of 40 years."
Gillies said the eight-year-old gelding was providing him with plenty of thrills and said he had been a very consistent horse.
"He was disappointing early on, but we were training him wrong and riding him wrong. Once we worked all that out and changed it, he has hardly ever run a bad race. We have had lots of fun out of him."
Earlier on Friday's Warrnambool card, former Kiwi Ablaze won the Star Printing Eulong Open Steeple (3200m), with last year's J.J. Houlahan Hurdle (3200m) and Jericho Cup (4600m) winner cruising to a four-and-a-half length win as a $1.22 favourite.
"The boys bought him as a horse for the Grand Annual Steeplechase (5500m) and he is certainly going the right way," Ciaron Maher, who trains in partnership with David Eustace, said."His flat form is outstanding and that was his first go over the bigger ones (jumps) and he has taken it with relative ease."