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“Small-Time Player” from Ontario Ready to Take on the Big Guns in Breeders’ Cup Betting Challenge

September 20, 2017

Story by Eric Wing

TORONTO, October 20, 2017 – When Whitby, Ontario native Chris Littlemore decided to enter the September 16 Woodbine Mile Handicapping Tournament, his goals were modest—even as he found himself leading the event with just a few races to go.

“My goal was to stay in the top five,” said the soft-spoken 57-year-old retired General Motors autoworker. “I consider myself a small-time player.”

At the Woodbine Mile event, Littlemore got caught late by winner Ali T. Aksoy, but stayed ahead of everyone else and earned over $8,500 in cash plus a coveted, fully-paid entry (worth $10,000 U.S.) in the November 3-4 Breeders’ Cup Betting Challenge (BCBC) at Del Mar. For Littlemore, this November will mark his second BCBC appearance, having played for the first time last year when he got off to a good start, then had a difficult Day 2 that saw him drop back to the middle of the pack.

“It’s hard to feel comfortable there seeing all the big names in the field,” he said. “This year, I hope to be a bit more brave in my decision making. That comes with experience. At a tournament like the BCBC, people are unafraid to go all in at any moment. Some guys are fearless. I’m not sure I’m at that stage yet. But I’m a competitive guy.”

And he’s also been a successful guy—even against deep, international fields of contest players. His 2016 BCBC entry was won by virtue of winning the 2016 NHC Consolation tournament when Littlemore bested more than 400 players on the event’s third and final day. It was a performance made even more impressive given that, a mere five years earlier, Littlemore wasn’t even aware that contest play existed.

“I had been playing the horses for 30 years, and had an account with Woodbine,” he recalled. “Then one day I saw that they were running contests so I entered a couple, had fun, and managed to come in eighth in one of them. One of the other contestants there asked me if I played online and all I could say was ‘Huh?’ I wasn’t aware of those either. Now I pretty much play contests full time.”

And the self-described “small-time player” continues to do well in them. He’s qualified for the last four NHCs and at the NHC’s most recent renewal last January, he finished 29th in the field of more than 550, earning $6,500 (U.S.). But he still picks his spots carefully.

“Some of the more expensive tournaments are out of my price range. As a result, I don’t play in too many live-money tournaments,” Littlemore said. “And they’re tough. You’re in against some major league handicappers.”

Littlemore is nothing if not modest. But there are also some little indicators out there that suggest a major tournament like the Breeders’ Cup Betting Challenge could be well within his wheelhouse.

Early speed often wins more than its share of races in Southern California, and Littlemore is an unabashed fan of horses that race on or near the lead.

“Something has to be really eye-catching for me to like a deep closer,” he said.

But there are also some broader reasons to think that Chris may have a “little more” luck at a venue like the Breeders’ Cup.

“I like playing tracks where horses come in from all over the place,” he said. “Gulfstream in the winter is like that. So is Saratoga. And I guess the Breeders’ Cup is like that too. I can’t tell you why, but I just seem to see the race better for some reason when horses haven’t all run time after time against each other.”

Littlemore also comes from a place—Canada—that has produced a pair of NHC winners in Brian Troop and Ray Arsenault, and two Breeders’ Cup Betting Challenge champions in Tommy Massis and Peter Behr.

“We have some pretty good handicappers up here,” Littlemore said with characteristic understatement. “The racing is good at Woodbine, and it’s tough—it’s one of the hardest tracks to handicap, and that might be why we have quite a few top guys all in one spot. The handicapping talent may be a bit more spread out in the States.”

More and more, top handicappers throughout North America are finding their way into contests, just as Littlemore did some six years ago. For those contemplating an initial foray into contests, he has a simple piece of advice.

“Just play,” Littlemore said. “Pay attention to what the names at the top do, and try to get a feel for why they are at the top. Practice makes perfect. And some post-tournament study can come in handy. With online games, you can see what they chose and try to figure out why. If you want to do well, these people are your targets.”

You may not hear a lot of raucous cheering from Chris Littlemore when one of his horses crosses the finish line first at Woodbine—or Del Mar. You certainly won’t hear any self-aggrandizement. But he, too, has become a player to watch among the many skilled tournament contestants throughout North America.

“I’m a laid-back, quiet kind of guy,” he admitted. “But I like to compete.”


Story by Eric Wing from October 20, 2017 for

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