Hildebrand won the 2009 Indy Lights championship and came close to winning the 2011 Indianapolis 500, hitting the wall on the final corner of the race and crossing the line in second place.

In recognition of his impressive 2006 performance, Hildebrand won the Gorsline Scholarship and was elected to the AARWBA All American Auto Racing First Team.

That year he also competed in the final round of the A1 Grand Prix series for A1 Team USA at Brands Hatch, finishing 4th in the Sprint race.

Hildebrand spent three days testing for the Force India Formula One team in December 2009, at the Jerez circuit, in a car shared with Paul di Resta.

This allowed him to take a gamble during his last pit stop, stretching out his fuel load to an eventual lead on the final lap.

On the very last turn, he slid out of the racing lane and into the retaining wall while passing rapidly slowing Charlie Kimball, allowing Dan Wheldon to take the victory.

Despite the damage to his car – including the loss of a wheel – Hildebrand retained enough speed to cross the finish line in second place.

On October 16, 2011, Hildebrand was involved in a 15-car chain-reaction crash at Las Vegas Motor Speedway in the season-ending IZOD IndyCar World Championships.

He sustained an injured sternum and was transported by ground ambulance to a Las Vegas area hospital, where he was admitted for treatment.

[13] For 2018 Hildebrand was signed for by Dreyer & Reinbold Racing to pilot their car in the Indy 500 (their only entry of the season) and finished 11th.

On February 1, 2022, it was announced Hildebrand had entered the 2022 running of the event,[17] competing in the Open Wheel Class, driving a 2022 Dallara IR18 Evo IndyCar.

MIT granted a three-year deferral, but he eventually allowed it to lapse as he continued to pursue his racing career.