For the 2014 season, Carpenter competed in the oval races on the calendar, while Mike Conway competed for the team on road and street courses. On March 20, J. R. Hildebrand was hired to run the 2014 Indianapolis 500 with the team in the No. 21. The move to a shared drive paid off well for the team early in the year, with Conway winning the 40th Toyota Grand Prix of Long Beach, and Carpenter winning the Indy 500 pole for the second consecutive year. Carpenter's four lap average of 231.067 mph was the first Indy pole-claiming run in excess of 230 mph for 11 years. Unfortunately, he was involved in a crash with James Hinchcliffe on a late restart, finishing 27th. Later in the season, Carpenter won the Firestone 600 at Texas Motor Speedway, his first win since the 2012 triumph at Fontana.