[19] In 2016 he won the off-season Winter Heat Sprint Car Showdown championship at Cocopah Speedway.

[20] Stewart joined CJB Motorsports for the 2019 World of Outlaws season, replacing David Gravel;[21] he won the series's special event at Nashville's Fairgrounds Speedway,[22] but left the team at the end of the year due to a lack of chemistry.

[24] Choosing to return to competition instead, he signed to run ten races with Roth Motorsports;[25] after these events were cancelled due to the COVID-19 pandemic, Stewart ran the majority of the 2020 World of Outlaws season with the No.

[26] He won for the team at Williams Grove Speedway in the track's prestigious Summer Nationals,[27] and then at Lakeside Speedway in October,[28] in the first of two races in which he was substituting for David Gravel, who was competing in NASCAR Gander Outdoors Truck Series events, for Jason Johnson Racing.

[29] At the end of the 2020 season, Stewart announced his retirement from active competition, purchasing his home track, Port City Raceway, to promote races there.