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Wayne Hillis will be looking to pick up a bit more holiday money when he heads to Sydney on Tuesday with his talented three-year-old filly Imelda Mary.

The Matamata trainer is pressing ahead with a start in the G1 Australian Oaks (2400m) at Randwick on Saturday with Imelda Mary, who has just completed her local campaign as joint New Zealand Bloodstock Filly of the Year with Queen Of Diamonds.

It will be Hillis’ second attack on the Australian Oaks and it comes 15 years since he saddled up G2 winner Boulevardofdreams to finish third to Wild Iris in the three-year-old fillies’ feature after a fresh-up fifth in Sydney in the Arrowfield Stakes (2000m).

Hillis and Boulevardofdreams then regrouped and headed on to America, where the daughter of Daggers Drawn made a hit-and-run bid on the G1 American Oaks (2000m) and finished a creditable seventh.

America will again be the focus of Hillis’ international attention after this year’s Australian Oaks, but not for Imelda Mary.

While Imelda Mary will head to the spelling paddock after her Sydney raid, Hillis will be counting down to a 28-day tour co-hosted by Taranaki trainer John Wheeler and his wife, Linda, taking in the last two legs of the American Triple Crown.

“I leave for the tour on May 15 and it would be great to pick up some more spending money beforehand,’’ Hillis said.

‘’I think she can get some of it in the Oaks. The race has always been in the back of my mind and I’m just overlooking her last run.’’

Imelda Mary, who is named after Hillis’ mother, is a dual Group Two winner who followed up her latest win at that level with a third in the Gr.2 Lowland Stakes (2100m), but then beat only four home in the Gr.1 New Zealand Oaks (2400m) at Trentham last start.

‘’She wasn’t happy in the ground and the way the race was run, a stop-start affair, didn’t suit her,’’ Hillis said. ‘’The three best credentialled fillies were all out of the money in it and we’d beaten the winner (Sentimental Miss) a couple of times before.”

Hillis will be out to continue a trend of having picked up prizemoney on most occasions he has taken horses to Australia.

In 2009 he won the Gr.3 Queen Elizabeth Stakes (2500m) at Flemington with Sterling Prince, who was also placed on that trip, and Izonit was runner-up in the 2010 Gr.2 Hollindale Stakes (1800m) in Queensland, while four years earlier Group One winner Dezigna was placed in each of his five starts in a Queensland campaign.

After the Australian Oaks, Hillis will have one further major mission before his holiday and that is a tilt at the Gr.2 Manco Easter Handicap (1600m) at Ellerslie later this month with Watch This Space, who was an unlucky last-start second to Volpe Veloce in the Gr.2 Japan New Zealand International Trophy (1600m) at Tauranga.

“He was held up a bit at Tauranga and if he had got out sooner it would have made it interesting,’’ Hillis said. ‘’He’s come through the race well.”