Jeff's first full Winston Cup season was 1993. During Speedweeks at Daytona in February, the rookie driver won the Gatorade 125 mile qualifying race; a win that shocked the motorsports world at the time. In the Daytona 500, he finished a strong fifth. However, his rookie season would be an up and down year. A combination of mechanical failures and accidents eliminated Jeff from more than a few races. At North Wilkesboro in April, Jeff spun backwards into the wall. The car soon caught fire; Jeff escaped before the car was engulfed by the flames. In mid-summer, the engine blew in three consecutive races. He did have a number of strong runs in 1993. In the non-points Winston Open event, Jeff jumped out to the lead and looked like he would transfer in the Winston Select all star race. However, in turn three at Charlotte, he lost the car and crashed. In the Coca Cola 600, he finished second and followed that up with another runner-up finish a few weeks later at Michigan. During his rookie season, Jeff struggled at Dover. The length of the races had him "falling out of the seat" in the last 100 laps.s Today, through experience and conditioning, Gordon usually dominates at the Delaware oval. In October at Charlotte, Jeff captured his first career pole position earning a spot in the 1994 Busch Clash. He finished the year 14th in the points standings and won the rookie of the year award. Off the track, Jeff spent most of his time dating Brooke, one of the Miss Winston ladies. There is an unwritten rule that the drivers can't date the Winston representatives. So, Jeff and Brooke got used to using the stairs instead of the elevator to avoid the NASCAR crowd.