The 2019 season saw improvement in Bowman's finishes, including three consecutive second-place finishes at Talladega, Dover, and Kansas. Bowman also made the starting grid of the 2019 Monster Energy NASCAR All-Star Race by winning the Fan Vote. It was announced on June 12, 2019, that Nationwide Insurance would not be sponsoring Hendrick Motorsports or the No. 88 after 2019, ending a five-year relationship prematurely. At the 2019 Camping World 400 at Chicagoland Speedway, Bowman held off a late charge from Kyle Larson to win his first career NASCAR Cup race. On June 13, 2019, Nationwide Insurance announced the end of their five-year sponsorship of the No. 88 after the 2019 season. On September 20, tool company Cincinnati Inc. signed a 10-year partnership deal with HMS, including primary sponsorship of the No. 88. He went to get eliminated after the Round Of 12 in the playoffs and finished 12th in the standings with one victory.