Kenseth made an agreement with his father Roy that Roy should buy a car and race, and Matt would work on the car until he was old enough to race. Matt began stock car racing in 1988 at the age of 16, and won the feature in his third night of racing. He started racing at Columbus 151 Speedway and Jefferson Speedway near Cambridge. After graduating from Cambridge High School, Kenseth worked for four years selling and shipping parts for Lefthander Chassis, a late model racecar chassis manufacturer just south of Wisconsin in Illinois.[1] Kenseth made a name for himself while driving at several Wisconsin tracks for Mike Butz in the #8 late model, beating nationally known drivers such as Dick Trickle and Robbie Reiser. He won the 1994 Slinger Nationals at Slinger Super Speedway. He won the 1994 and 1995 track championships at Wisconsin International Raceway. He also won track championships at Madison International Speedway, including the 1994 late model track championship over Robbie Reiser. Kenseth's last shop in Wisconsin was at Gerry Gunderman's American Speed Association shop, who was also Alan Kulwicki's last shop in Wisconsin before moving to NASCAR. Kenseth decided to go south to the USAR Hooters Pro Cup series in 1996 and nearly won the series championship as a rookie.