The 98th Indianapolis 500 was held at the Indianapolis Motor Speedway in Speedway, Indiana on Sunday May 25, 2014. It is the premier event of the 2014 Verizon IndyCar Series season. Tony Kanaan entered the race as the defending champion. Ed Carpenter won the pole position, his second consecutive pole at Indy. The race was won by Ryan Hunter-Reay, the first American-born winner since Sam Hornish, Jr. in 2006. Hunter-Reay held off second place Hélio Castroneves by a margin of 0.0600 seconds, the second-closest finish in race history. At an average speed of 186.563 mph (300.244 km/h), it was also the second-fastest 500 in history. Marco Andretti, Carlos Muñoz, and Juan Pablo Montoya rounded out the top five. Kurt Busch, in sixth position, claimed Rookie of the Year honors.

The month of May activities opened with the inaugural Grand Prix of Indianapolis, which was won by Simon Pagenaud on May 10. Practice opened for the Indy 500 on Sunday, May 11. Time trials were held over two days, May 17–18, and a post-qualifying practice was held on May 19. The traditional final day of practice, dubbed Carb Day, was held on Friday, May 23.

All four divisions of the Road to Indy ladder participated in the month of May activities. The Cooper Tires Indy Lights held the Liberty Challenge and Freedom 100. The Pro Mazda Series and U.S. F2000 held races on the Speedway's road course, then held oval races at nearby Lucas Oil Raceway. The Speed Energy Formula Off-Road series also held an event on Carb Day.

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