ETOBICOKE, Ontario – Trainer Catherine Day Phillips recorded a career high in wins at Woodbine in 2016 with 22 victories from 84 starters, highlighted by her first win in the Woodbine Oaks with Neshama. While those accomplishments might be tough to top in 2017, Day Phillips would be off to a great start if Guy Caballero gives her a first victory in the Queen’s Plate here on July 2. Day Phillips has had five starters in the Queen’s Plate, the first jewel of the Canadian Triple Crown, and two finished second. A Bit O’Gold couldn’t catch Niigon in the final strides of the 2004 Queen’s Plate and went on to win the final two legs of the Canadian Triple Crown – the Prince of Wales and Breeders’ stakes – and win three graded stakes at 4. Mr. Foricos Two U was caught in deep stretch by Eye of the Leopard in the 2009 Queen’s Plate. Day Phillips described the two losses, by three-quarters of a length and a neck, as “heartbreaking.” “A Bit O’Gold was particularly heartbreaking because he was such a good horse,” she said. “He was such a good 2-year-old, a very good 3-year-old, and he proved what type of horse he was at 4. I felt he really did deserve it. Mr. Foricos Two U was a little bit different. The stars aligned, and everything came together. He had an absolutely brilliant day. It was a great ride by Mike Smith, and he was unlucky not to win.” Queen's Plate pedigree profile: Guy Caballero Day Phillips’s last Queen’s Plate starter came in 2011, when Head Honcho finished eighth behind Inglorious. But this year, she’s hoping her luck will turn with Guy Caballero. “We missed a few years, but we’re back,” she said. “We have some nice horses, and fingers crossed.” Bred in Ontario by Sean and Dorothy Fitzhenry, Guy Caballero was bought back by his breeders out of the 2015 Keeneland September yearling sale and immediately went to Day Phillips to prepare for his racing career. He wintered at Day Phillips’s farm in Maple, Ontario, before joining her at the track last year as a 2-year-old. Day Phillips said the son of Quality Road had a mind of his own during his juvenile campaign. “He was a little bit quirky as a 2-year-old,” she said. “His nickname was Chaos because whenever he went down the shed row, everybody scattered daily for months and months on end.” When it came to racing, however, Guy Caballero channeled his energy the right way, winning in just his second start. Following his maiden win, Guy Caballero stepped up to face stakes company for the final two starts of his 2-year-old campaign in the Coronation Futurity and Display Stakes. He finished fifth in the Coronation Futurity and third in the Display and appeared to tug at jockey Rafael Hernandez early in each race while sitting just off the leader. :: QUEEN’S PLATE WATCH: Alex Campbell and Ron Gierkink’s Top 10 contenders, video, and more Guy Caballero took the winter off back at the farm, and Day Phillips said a key component of his training this spring has been learning to sit behind horses. “I agree he was a little bit keen towards the end of his 2-year-old year,” she said. “We’ve been quite mindful to teach him and let him learn to relax and stalk horses a little bit and move when he’s told to. We’ve worked a lot in company all spring, and he’s really responded well. He sits nicely and then makes his move when called upon, and that’s translated into his first race this year. He was much more settled.” Guy Caballero made his 3-year-old debut in an allowance race here May 7. Instead of tugging at Hernandez early, Guy Caballero came from off the pace in the seven-furlong sprint, finishing second to Conquest Lemonraid. “He definitely wants to go two turns, but it was a good place to start,” Day Phillips said. “I thought it was a very encouraging race.” Guy Caballero has options moving forward. He could be entered in an allowance race for 3-year-olds over 1 1/16 miles on Tapeta on June 4 or wait another week to run in the $125,000 Plate Trial over 1 1/8 mile for Canadian-bred 3-year-olds on June 11. Day Phillips said a decision on which spot to run in will be made following his next work, but for now, she is pleased with how Guy Caballero is progressing toward the Queen’s Plate. “I think the most important thing I see with him is he’s improving,” she said. “Everything wasn’t all there in his first race, but he needed the race, and he needed to get going. For me, that’s what I’ve been most encouraged by, is that he’s an improving horse.”