"It was a life-changing day for me," recalled Gwynn.
The Miami native collided with a wall at high speed and his car was engulfed in flames. He lost his left arm and was paralyzed, forced to move around in a wheelchair ever since.
But this past weekend, 21 years later, Gwynn got back in a car and raced for the very first time since the crash.
"My whole family was there, my mom and my dad, my wife, my daughter," said Gwynn. "That's the first time she's ever seen me race competitively, so it was a very emotional weekend for all of us."
The three-race exhibition in Gainesville pitted Gwynn against legendary driver Don "Big Daddy" Garlits. It was held at the Gator-nationals, the site of Gwynn's last professional victory.
"You had to stay focused because you want to win the race," said Gwynn, "but you didn't want to be crying pulling into the startling line, you know?"
Gwynn was able to race again thanks to a custom built dragster that he and Garlits both used. It has no steering wheel, no gas pedal, no brake pedal, just a joystick -- the same kind that steers Gwynn's wheelchair.
"The car is quite a bit slower than my racing days," Gwynn laughed. "Instead of going 300 miles per hour, it was going more like 30 miles per hour, but it was still a competition."
And Gwynn was racing to win. He didn't want to disappoint the 50,000 fans who showed up. So after losing the first two races, he returned to old form and crossed the finish line in first place.
"Any day is a good day when you beat Big Daddy!" he exclaimed.
And making it a better day, the charity race weekend raised more than $200,000 for the Darrell Gwynn Foundation, which donates wheelchairs to those in need.
Follow Adam Kuperstein on Twitter at @akuperstein.