| | Heat | Dash | B Feature | A Feature |
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| 5/11/2019 | Plymouth Speedway - Plymouth, IN Saturday Night Event DIRTcar UMP Modifieds, Stock Non-Wing, Street Stocks, Winged Crate Sprints | Rain Out |
| 6/13/2019 | Kankakee County Speedway - Kankakee, IL DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals Dirt Super Late Models | Results | | Dylan Caldwell (DIRTcar UMP Modifieds) | 6th | - | 3rd | - |
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| 7/6/2019 | Plymouth Speedway - Plymouth, IN Saturday Night Event DIRTcar UMP Modifieds, Stock Non-Wing, Street Stocks, Winged Crate Sprints | Results | | Dylan Caldwell (DIRTcar UMP Modifieds) | 4th | - | 2nd | 10th |
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| 10/19/2019 | Kokomo Speedway - Kokomo, IN Kokomo Klash XIII A Modifieds, Street Stocks, Dirt Late Models, Hornets, Super Stocks | Results | | Dylan Caldwell (A Modifieds) | 8th | - | 3rd | - |
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