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Shane Jackson will chase his biggest success as a trainer when he saddles Mystery Island in the Warrnambool Cup.

Former Irish jockey Shane Jackson won two of the feature jumps races at the Warrnambool May Carnival and now is after a major flat win as a trainer. 

Jackson won the Brierly Steeplechase on Gold Medals in 2018 and the Grand Annual Steeplechase in 2020 aboard Ablaze, however the Galleywood Hurdle eluded him. 

Since retiring from riding over jumps, Jackson has teamed with Warrnambool trainer Lindsey Smith as his assistant-trainer while also dabbling in training a few in his own right. 

Jackson's team includes Japanese-bred Mystery Island who is set to contest the major flat race at the three-day Carnival, the Listed Warrnambool Cup (2350m) on Thursday. 

Mystery Island has provided Jackson with his two sole winners (from 31 starters) since taking out his trainer's licence, scoring at Bendigo over 2200m last May and over the 1700m course at Warrnambool in December. 

The gelding was transferred into Jackson's care in time for last year's Warrnambool Cup, in which he finished eighth, when not suited on the very heavy ground. 

A fine Warrnambool Carnival this year, a rarity, has Jackson excited at Mystery Island's prospect, especially if the track continues to dry out. 

"He likes better ground," Jackson said. 

"All of his runs this campaign, except for his last one, have been superb. 

"I would just forget about the Mornington Cup. It was run at a very strong tempo, and he had to make a long run and he's possibly not up to those stronger stayers. 

"If the track dries out, he's definitely a good chance." 

Mystery Island finished ninth in the Listed Mornington Cup (2400m) on April 20 and Jackson said this distance range was ideal for the gelding. 

But the track condition is the key. 

"He ran in the Warrnambool Cup last year and the track was quite wet and shifty," Jackson said. 

"It's not that he doesn't go on it, he doesn't quicken off it." 

Jackson may not have the same riding record as champion jumps rider Steve Pateman, who has also trained a few winners, but to train a major winner at the Warrnambool Carnival would be a feather in his cap. 

"I've only had two winners to my name so any winner is a good winner, but a Warrnambool Cup would be a dream come true," Jackson said. 

"It's not going to be easy, but he's in good order and we're hopeful."