Matt began his racing career driving sportsmans at the age of fifteen at Jefferson Speedway, a local 1/4 mile track. He soon graduated to the larger, more powerful Late Model cars at Madison International Speedway, Wisconsin's fastest 1/2 mile. Matt made a deal with his dad when he was 13 that he would work on the Sportsmans cars that Roy drove until he turned 16 at which point Matt could drive. After seeing the way his son drove, Roy stepped out of his car and concentrated on Matt's racing. Matt worked at Lefthander Chassis in Rockford IL for 3 years where he gained valuable experience in chassis and shock setups.

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He became the youngest driver to win an ARTGO feature, on 6/19/91 at LaCrosse Fairgrounds Speedway in Wisconsin.

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He placed 2nd in overall points at MIS to Robbie Reiser, his future car owner and crew chief.

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Madison International Speedway Champion
He won 10 of 17 regular features and never finished lower then 5th
WIR-Kaukauna track champion, a fast "D" shaped half mile track between Green Bay and Appleton.
Overall winner of the Miller Genuine Draft Nationals -- a prestigious event split between Slinger Speedway and MIS
He added his name to a list of well known drivers including, Rich Bickle, Dick Trickle, Mark Martin and the Late Alan Kulwicki.

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Placed 2nd in overall points at MIS Track champion at Kaukauna for the second year in a row, driving the Mike Butz Racing #8

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Matt moved to Huntersville, N.C. to drive for Carl Wegner in the Hooters Cup Series
Placed 3rd in overall points, coming close to a championship at the last race
He ran his first Busch Grand National race at Charlotte Motor Speedway in a rented car, placing 31st
Matt was hired by Gerry Gunderman in November and moved back to WI to race for the All Star Racing Team
This is probably the best team in ASA. Matt ran the last race of the ASA series and placed 3rd.

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Matt was hired by Robbie Reiser to replace the injured Tim Bender in the Kraft Singles #17 Chevrolet
The initial deal is for 6 races. Matt Qualifies 3rd and places 11th in his very first race with the #17 Busch car
The following week he places 7th at Talladega. Matt is signed for the rest of the season
Places 22nd in Busch points, having missed the first nine races. 21 starts, 2-top fives and 7-top tens
Mark Martin shows interest in Matt and Jack Roush hires Matt to be a test driver for the new Ford Taurus Winston Cup car
Matt tests a Winston Cup car at Darlington and Talladega.

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A big sponsor bails out of their deal just days before the first race at Daytona. Lycos signs up for a one race deal. Matt finishes the race in 6th. A week later at Rockingham, the Lycos decals are back on the car as a way to say thank you, Matt wins the race and a one year contract with Lycos is soon accomplished.
Matt attempts his first Winston Cup start at Talladega in a Jack Roush #60 car. The Roush restrictor plate cars are pretty slow and Matt fails to make the race. The 98 BGN points battle is a 3 way race with Matt, Dale Earnhardt Jr. and Mike McLaughlin.
Matt gets his first Winston Cup start when Bill Elliott`s father passes away just before the Dover race
Matt dominates the BGN race on Saturday then climbs in the #94 Cup car and finishes a very impressive 5th
This finish beats a record for best finish in a Winston Cup debut held by Rusty Wallace since 1980.
Matt finishes the season 2nd in points to Dale Earnhardt Jr, just 48 points shy of the Championship.

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Matt lands a great sponsor in DeWALT Tools with Kraft and Luxaire Heating and Cooling as Associate sponsors. Matt's first win of the season at Darlington is followed by a 10th place finish the next day in Bobby Labonte's Cup car. Bobby broke his scapula during Busch practice and Matt relieved Bobby early in the race, taking the #18 Pontiac from the back of the field to 10th place in his 2nd Cup race.

Announced that Mark Martin & Jack Roush will be the owners of Matt's Winston Cup Team, to be debuted later this year at Michigan, carrying the Dewalt colors into Winston Cup action.

Visine will be the new sponsor of the #17 Chevrolet Busch car to be driven by Matt Kenseth and Jason Schuler in the year 2000.