On March 27, 2018, it was announced that Windom would make his
Indy Lights debut driving for
Belardi Auto Racing in the
Freedom 100 at the
Indianapolis Motor Speedway with support from
Jonathan Byrd's Racing, the same group that supported fellow sprint car driver
Bryan Clauson venture into Indy Lights and the
IndyCar Series. Windom, however, crashed during the first morning testing session on May 21 and the damage to the car forced Windom to withdraw from the event. On April 16, 2019, it was announced that Windom would again attempt to make his Indy Lights debut in that year's Freedom 100 with Belardi Auto Racing and Jonathan Byrd's Racing. The day before the race, Windom suffered a massive crash during the
Hoosier Hundred; however, Windom still decided to start the race. Unfortunately, Windom would experience another harrowing crash on the first lap of the Freedom 100 after he hit the spinning
David Malukas and climbed atop the
SAFER barrier. Neither driver was injured. ==Motorsports career results==