He remained with Penske for the 2014 season. Castrovenes finished third at the season-opening Grand Prix of St. Petersburg and the Grand Prix of Indianapolis three races later. He qualified fourth for the Indianapolis 500, and finished second, 0.0600 seconds behind Hunter-Reay in the second-closest finish in event history after a late race duel for the victory. He took pole position for the first Detroit Belle Isle Grand Prix race and won the second. After three straight sub-par results, Castroneves finished second in the Pocono IndyCar 500 at Pocono Raceway to tie his teammate Will Power for the points lead, which took after finishing eighth in the Iowa Corn Indy 300. He relinquished the points lead after a throttle problem left him 19th in the Honda Indy 200 at Mid-Ohio. Entering the final race, the MAVTV 500 IndyCar World Championships, Castroneves was 51 points behind Power. After winning the one point for the pole position, he had to claim victory and for Power to finish seventh or lower to become the champion. Castroneves placed 14th for second overall with 609 points.