DCR owner Dale Coyne took up an option to retain Wilson for the 2014 season after recovering from injury and recommenced training. Michael Cannon became his race engineer after Bill Pappas moved to Rahal Letterman Lanigan Racing. Coyne promised Wilson better resources for him to continue achieving top-ten finishes. His first top ten-finish of 2014 was a sixth at the Indy Grand Prix of Alabama. Wilson started 14th at the Indianapolis 500 finishing eight places lower and two laps down in 22nd after debris damaged his front wing late in the race. One race later, Wilson achieved a season-best fourth at the Detroit Belle Isle Grand Prix and four top-ten finishes in the final 12 rounds for 15th overall with 395 points.