Toronto resident Michael Cavalaris captured the $19,575 first prize in the 2010 Woodbine Thoroughbred Handicapping Challenge, held at Woodbine Saturday through Sunday.

“It feels fabulous,” said Cavalaris. “You sort of dream about this kind of thing happening to you, but you never believe it’s ever going to happen. It’s a wonderful feeling to win. I’ve been in it every year since its inception.”

Michael Cavalaris, 50, has been around the racetrack his entire life, having worked in the 1970s for his father, Hall of Fame conditioner Lou Cavalaris, Canada’s Most Outstanding Trainer in 1976.

“He’ll be thrilled when he finds out I won the contest,” said Michael Cavalaris. “He’s one of the greatest trainers that ever trained a horse. He obviously factored into this win with all his knowledge and guidance.

“He’s doing very well. He’s up and watches the races every day. We talk about it. This is what we have in common. This is what adds meaning to our lives other than our day-to-day thing.”

The thoroughbred contest, which costs $330 to enter, asks participants to handicap several race cards and come up with $2 win-place wagers on 10 different horses on each of Saturday and Sunday.The player with the highest return from the 20 wagers is the winner of the contest. Each contestant must make three of each day’s 10 wagers on a pre-determined mandatory race.

Cavalaris believes he won the contest on the strength of his selections in the mandatory events. He correctly selected the winner of four of the six mandatory events, including Ontario Colleen longshot Barracks Road ($20.50, $11.30) and Travers outsider Afleet Express ($16.10, $7.70).

“There are days you can do nothing right and there are days you can do nothing wrong,” said Cavalaris. “It’s a lot of luck. The stars were aligned.”

In total Cavalaris won with a score of $185.20. He received a free entry into this weekend’s challenge by finishing second in a similar challenge held at the Greenwood Teletheatre in the spring. Pending a 72-hour audit period, in addition to first-place prize of $19,575, Cavalaris received $1,500 for being second at the half-way point. He also receives a berth in the 2011 DRF/NTRA National Handicapping Challenge (NHC) in Las Vegas – the same event captured by Barrie resident Brian Troop earlier this year.

The Woodbine contest’s second-place finisher Steve Duffield ($179.10 final score) and third-place finisher Eugene Yakura ($176.60) have also earned berths in next year’s NHC.