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Main Stage and Johannes to prove the headline acts

David Jennings continues his attempt to turn $100 into $1,000 in Australia

Johannes Vermeer: just denied by Gailo Chop in the Caulfield Stakes
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Fancy seeing an Aussie racing rookie turn $100 into $1,000 during his stint at the Spring Carnival? Well, stay tuned.

I have never been to Australia before, never studied Australian form before and not sure of who or what to watch out for – yet the mission is most definitely possible. The toughest challenges are always the best ones.

I have been given $100 in the hope that it will turn into $1,000 by the time I fly back to Dublin on November 11. The journey continues at Caulfield on Saturday with two wagers. 

The challenge got off to a stuttering start last Saturday, and that's an understatement. First bet: $10 on Aloft – finished ninth of ten. Second bet: $10 on Riven Light – finished seventh. Third bet: $10 on Catchy – finished third. The only way is up. Those setbacks have made me study harder.

It is Caulfield Cup day on Saturday and I have now realised you can watch every Australian race for free online on Watch out bookmakers, here I come.

Hours have been spent studying Saturday's showdowns and I think I have found a good thing in the Group 3 Ladbrokes Classic (4am BST) in the shape of Main Stage.

This three-year-old somehow snatched victory from the jaws of defeat at Flemington last time, where he arrived with a wet sail down the outside to collar Cliff's Edge close home. He was last turning into the short home straight and showed awesome speed to edge in front where it mattered. 

He is stepping up 200 metres in trip and that should be right up his street. Cliff's Edge is better off at the weights this time but Main Stage won with more authority than the winning margin suggests at Flemington. He can win again so let's have $25 at 11-4. Defeat is not to be contemplated. 

The main event itself is due off at 6.30am. It is the Caulfield Cup and it can go to Ireland for the first time. This is not my heart ruling my heart. This is my heart and my head agreeing with each other. 

Johannes Vermeer caught many an eye with the way he flew home in the Ladbrokes Stakes last Saturday and the step up in trip should suit. He's drawn stall two and, with Wicklow Brave and Lord Fandango in the line-up, he should be able to get the brisk tempo up front that he needs.

I feel that Johannes Vermeer is the most talented horse in the race and, if the gaps open on the home bend, he can ensure that Aidan O'Brien wins a 25th top-tier event this year and thus equal Bobby Frankel's record. 

Could I have $20 on Johannes Vermeer at 7-2? Thank you very much. 

Thousand Dollar Challenge bets

Main Stage
4am Caulfield, Saturday
$25 win at 11-4

Johannes Vermeer
6.30am Caulfield, Saturday
$20 win at 7-2

Balance: $25

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This is not my heart ruling my heart. This is my heart and my head agreeing with each other
E.W. Terms
Sky bet