Better chance of winning

Ride a horse that is "A" or "B" rated with a lot of stamina that prefers to be at the back of the pack. When you are about 5 furlongs away from the finish line, start pressing the Triangle button to get closer to the front. Use most or all of your stamina before letting the horse run out to the leaders. It doen't always work, but it's the best strategy we've found so far.