Almirola was named co-driver of the No. 8 United States Army-sponsored Chevrolet for the 2008 Sprint Cup Series, sharing the ride with Mark Martin. His best finish during the season was an eighth-place finish in the 2008 Food City 500 at Bristol, and his best start in Sprint Cup was a third-place start at the 2008 Goody's Cool Orange 500 at Martinsville. Almirola was named the full-time driver of the No. 8 for the 2009 season. Seven races into the 2009 season, Almirola lost his ride due to a lack of sponsorship. He later signed a five-race deal with Key Motorsports to drive their No. 40 Chevrolet Impala SS in the Nationwide Series. He returned to the Truck Series, driving part-time in the No. 15 Graceway Pharmaceuticals-sponsored Toyota Tundra for Billy Ballew Motorsports, and had a seven-race streak of finishes eighth or better. He also made one attempt and one race in the No. 09 Phoenix Racing Chevrolet in the Sprint Cup Series.