In 2014, Carpenter decided to split driving the No. 20 with Mike Conway; Conway drove the road courses and street circuits while Carpenter drove the ovals. At Carpenter's season debut, the Indianapolis 500, Carpenter qualified on pole position for the second consecutive year. In the race, Carpenter, Ryan Hunter-Reay, Hélio Castroneves and Marco Andretti dominated the lead with Carpenter leading for 26 laps. On lap 176 on a restart for separate crashes between Scott Dixon and Josef Newgarden, Carpenter was running 2nd to Hunter-Reay when Townsend Bell went three wide in an attempt to pass Carpenter on the outside while James Hinchcliffe was on the inside of Carpenter. Hinchcliffe made contact with Carpenter, sending both of them into the wall. This ended Carpenter's race with a 27th-place finish. At Carpenter's next race, the Firestone 600 at Texas, he qualified 5th and soon battled with Will Power for the lead. Later, when Carpenter and Power were making pit stops, Power came into the pit lane too fast and had to serve a penalty. On lap 142 a caution came out for Takuma Sato who had an engine fire. Carpenter and 2nd place driver Juan Pablo Montoya stayed out while the remaining lead lap cars – Power, Simon Pagenaud, Dixon and Tony Kanaan – pitted to get new tires. On the restart, with three laps to go, Carpenter held off Power for his third career IndyCar Series win.