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My First Woodbine Win: Catherine Day Phillips

February 11, 2026

Catherine Day Phillips is a multiple graded stakes-winning trainer. She comes from a long line of accomplished horse people. Her father, Jim Day, and her late mother, Dinny Day, were both trainers. Her grandparents, Charles and Janet Burns, founded Kingfield Farms in 1946. Day Phillips began her training career in 1994. She has recorded 47 career stakes wins and over $24 million in lifetime purse earnings. The stable’s greatest success stories include A Bit O’Gold, who was Canada’s Horse of the Year in 2005, and Hall of Famer Jambalaya, who provided Day Phillips with her first Grade 1 win in the 2007 Gulfstream Park Breeders’ Cup Turf Stakes.  In the same year, he won the Arlington Million Stakes, making Day Phillips the first Canadian and the first woman to win the Grade 1. Other stars include Mr Havercamp, Dixie Moon, Geraint, and Millie Girl. Day Phillips was a finalist in the 2017 Sovereign Awards in the Outstanding Trainer category.

Catherine Day Phillips (Michael Burns Photo)
Catherine Day Phillips (Michael Burns Photo)

Day Phillips’ first Woodbine win came on June 23, 1994, in Race 5, with Gentleman Artist. Sandy Hawley was the jockey, and Kingfield Farms owned and bred the horse.

What first comes to mind about your first win at Woodbine?

“My first win was exciting because the horse was a homebred and he was owned by my grandmother, Mrs. Janet Burns. He was one of the first out of four horses that I had when I first started training in 1994.  We took the four horses to Florida, and I was stabled at Sam-Son Farms in Ocala. Gentleman Artist ran once in Tampa, which was a bit of a mess, and then we shipped up to Woodbine. He was third in his first race at Woodbine, and then he came back and won.  Hall of Fame jockey Sandy Hawley was on him. My father, Jim Day, was in the winner’s circle along with Woodbine trainers Elizabeth Elder, Barb Minshall, and baby Chad Elder. Seeing the win photo again reminded me of how long ago that first win actually was!”

Gentleman Artist What do you remember about the race?

“More memorable than my first win with Gentleman Artist was our first start at Woodbine. He was very naughty in the paddock, and I also felt a lot of pressure for him to run well. He was awful to saddle; I remember after legging Francine up that even my kneecaps were sweating! Nothing was ever as stressful as saddling Gentleman Artist that day at Woodbine. He ran third and came back to win his next start. By then, both he and I were well-schooled, and the race went much smoother.”

What do you remember about Gentleman Artist?

“Sadly, he was claimed from us out of that race. It was a short and sweet time together. It was really special to have my first win with a horse that was owned and bred by my grandmother. She helped to kickstart my career as a trainer, and I will always cherish the early days and sharing those memories with her.”

What impact did that win have on your career?

“It felt like the first step. I envisioned a significant career as a racehorse trainer, and luckily, things have unfolded in that direction.”

When you look at the win photo or watch a replay of the race, what goes through your mind?

“Every journey starts with one step, and that was one of the first steps. I’m grateful for the years that have followed.”

Sophie Charalambous, for Woodbine

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