Fleming made his debut in 1988, driving the #40 Starrett Corporation Buick into the field at Darlington, qualifying 33rd. Fleming survived 'The Lady In Black' and finished race 28th, eight laps off the pace. Fleming made another goround at Rockingham, starting once again in 33rd, but finishing in the 24th position.
Fleming finished 24th again in his only 1989 race. This time he qualified 33rd at Charlotte. Despite finishing 24th, Fleming was seventy-one laps down.
Fleming's busiest year came in 1990, when he drove six races in route to a 51st in points. At Daytona, Fleming earned his first ever top-10 start, qualifying 9th. He then followed that up with a 20th-place finish, a career best. Later in the year, Fleming would also add two 21st place finishes and a twenty-second. Fleming fell out of two races, but both were due to engine problems, making 1990 Fleming's best year.
Fleming closed out his car with a one-race deal in 1991. Driving at Orange County Speedway, Fleming qualified the #24 Ford into the field with a 27th place effort. Fleming was only able to improve to 26th, though, before falling out of the event.