Alyssa Phillips is a name you should get used to hearing.

The U25 ranked developing rider won the biggest event of her burgeoning career last month—the inaugural Lexington CCI4*-S at the Land Rover Kentucky Three Day Event—aboard a horse named Oskar. But the victory comes as no surprise to anyone who knows her. Phillips been on a winning streak for months now—and on multiple horses.

We caught up with the 24-year-old on her drive home from Kentucky to chat about the amazing year she’s had (yep, even in the times of COVID) and her fantastic journey to where she is today.

It’s a story that starts with a Western saddle and a friendly neighbour…

“I was maybe two when I started riding western,” said Phillips. “Our neighbor did barrel racing and it wasn’t until we moved into Fort Worth, Texas, when I started riding English. I was one of those kids who practically lived at the barn, it was called Curragh Equestrian Center and I would go to all the summer camps. I was a true barn rat.

Image courtesy of Alyssa Phillips.

“While I was in college, I called up a friend who was riding with five star competitor Jennie Brannigan—she said I really needed to come east. Now I had never actually met Jennie, but that didn’t stop my mom from calling her up and basically asking ‘can you take this girl and her four horses?’ That was in the fall of 2017.”

In June of 2019, Phillips won her first U25 3*-L at Bromont, ON. In her nine FEI appearances since, she’s won an astounding six events—across multiple FEI levels with multiple horses—and placed in the top ten of all but one.

“The Kentucky 4*-S was the biggest win of my career so far, but I have had a super run with a couple of young horses. [One is Cornelius Bo, a horse that came from 5* German rider Anna Seimer, who also competed in Kentucky; the other is FE Celestino.] Among others, we’ve won one and two-star events at Red Hills and StableView in the past year so I would say it’s been a pretty good year so far!”

The last time Phillips won at the Kentucky Horse Park, it was the 2011 FEI North American Young Rider Championships and she was 14, on a horse called “Sundance Bay.” That was one year before her dad passed away of cancer. In April, Phillips won in Kentucky again, taking home the Lexington CCI4*-S title, on her and Julie Phillips’ Oskar.

“Sundance Bay really gave me my break. He was 19 when we won at the Horse Park in 2011!” exclaimed Phillips. “He lived at Curragh Farm where I started riding and he taught the two daughters at the farm. Well, one day I wrote on a piece of note paper in the barn and said: “When you don’t want him anymore, I will buy him from you.” And that’s how I ended up riding him! Thankfully when it came time to retire him they were more than happy to have him back—he’s still there!”

Image courtesy of Alyssa Phillips.

In the Lexington 4*, Phillips and Oskar, whom she purchased from Liz Halliday-Sharp, made a huge leap up the scoreboard by managing to add just 5.6 cross-country time penalties to their dressage score. On a day where “just ride your plan” turned out to be impossible for many, it’s exactly what Phillips and Oskar went out and did—making them not only the fastest of the day, but one of the few to actually complete the course at all.

“I pulled up the livestream and was watching before my round,” said Phillips. “Everyone was leaving out strides and adding strides and they were all over the place, so I asked my coach, Jennie Brannigan, what I should do in the first combination. She said just set yourself up [for the log] and you’ll know what to do when you get there. With the rain the hardest part was seeing where I was going. Oskar made it all feel easy.”

It would appear Oskar, who apparently always show jumps better at events where the show jumping comes after cross country (“because it makes him tired and a lot more rideable!”) made it through the “5* of the 4*’s” just cruising.

Alyssa Phillips and Oskar. Photo by

Phillips and Oskar will next compete at Jersey Fresh in May for the 4*-L, and hope to head overseas to contest their first 5* sometime in the next year.