Sprague began racing in the Trucks' first year of competition in 1995. He began the season in the No. 31 Chevrolet Silverado for Griffin Racing, winning the pole at Louisville Speedway. After the Action Packed Racing Cards 150, Sprague switched to the No. 25 Budweiser-sponsored Chevy for Hendrick Motorsports. He ended the season with a pole at Phoenix International Raceway, and had three fourth-place finishes. In 1996, he slid over to the No. 24 Quaker State-sponsored truck owned by Hendrick, winning his first race at Phoenix, followed up by back-to-back victories at Nazareth Speedway and The Milwaukee Mile. With five wins total and two poles, Sprague lost the championship by 53 points. That season, he made his Winston Cup debut, running a pair of races in the No. 52 Pedigree Petfoods-sponsored Pontiac Grand Prix for Ken Schrader. He led two laps and finished 23rd in his debut at Phoenix, but wrecked the following week at Atlanta Motor Speedway.