From the world screen go to World Circuits>Americas>Daytona International Speedway>Custom Race>Tri-Oval.
Then once on the Race Settings screen Change laps to at 10 minimum, and change Tire Wear to X15 for faster wear after a few laps youll see red on your Tire gauge once you see that take a pit stop and don't skip the option for changing tires. One your pitstop is complete or shortly after entering the track the trophy will pop.