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| 2/2/2021 | Volusia Speedway Park - De Leon Springs, FL 50th Annual DIRTcar Nationals - Night #1 410 Sprints - Winged, DIRTcar UMP Modifieds | Results | | Jesse Rupe (DIRTcar UMP Modifieds) | 10th | - | 15th (DNF) | - |
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| 2/3/2021 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals $6,000 to win 410 Sprints - Winged: All Star Circuit of Champions DIRTcar UMP Modifieds | Results | | Jesse Rupe (DIRTcar UMP Modifieds) | 12th | - | 14th (DNF) | - |
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| 2/4/2021 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals $6,000 to win 410 Sprints - Winged: All Star Circuit of Champions DIRTcar UMP Modifieds | Results | | Jesse Rupe (DIRTcar UMP Modifieds) | 11th | - | 9th | - |
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| 2/5/2021 | Volusia Speedway Park - De Leon Springs, FL 50th Annual DIRTcar Nationals - Night #4 (DIRTcar UMP Modifieds Gator Championship Night 1) 410 Sprints - Winged: World of Outlaws DIRTcar UMP Modifieds | Results | | Jesse Rupe (DIRTcar UMP Modifieds) | - | - | - | 5th |
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| 2/7/2021 | Volusia Speedway Park - De Leon Springs, FL 50th Annual DIRTcar Nationals - Night #6 (DIRTcar UMP Modifieds Gator Championship Night 3) 410 Sprints - Winged: World of Outlaws DIRTcar UMP Modifieds | Results | | Jesse Rupe (DIRTcar UMP Modifieds) | 9th | - | 12th (DNF) | - |
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| 2/8/2021 | Volusia Speedway Park - De Leon Springs, FL 50th Annual DIRTcar Nationals - Night #7 (DIRTcar UMP Modifieds Gator Championship Night 4) DIRTcar UMP Modifieds, DIRTcar Pro Late Models | Results | | Jesse Rupe (DIRTcar UMP Modifieds) | - | - | DNS | - |
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| 5/8/2021 | Ultimate Motorsports & RV Park - Elkin, NC Southeast Dirt Modified Series DIRTcar UMP Modifieds, Street Stocks, Dirt Late Models, Pony Stock, Baby Grand, Pure Stock | Results | | Jesse Rupe (DIRTcar UMP Modifieds) | 2nd | - | - | 3rd |
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| 6/5/2021 | Portsmouth Raceway Park - Portsmouth, OH Complete Racing Program DIRTcar UMP Modifieds, Dirt Late Models, Economy Late Models, Limited Sport Mod | Results | | Jesse Rupe (DIRTcar UMP Modifieds) | 5th | - | - | 20th |
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| 8/14/2021 | I-77 Speedway - Ripley, WV Dirt Super Late Models, DIRTcar UMP Modifieds, B Modifieds, Street Stocks, Enduro | Results | | Jesse Rupe (DIRTcar UMP Modifieds) | 2nd | - | - | 4th |
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| 9/11/2021 | Willard Speedway - Willard, KY Dirt Super Late Models, DIRTcar UMP Modifieds, DIRTcar Sport Compact, Limited Sport Mod, Dirt Crate Late Models | Results | | Jesse Rupe (DIRTcar UMP Modifieds) | 3rd | - | - | 4th |
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| 10/2/2021 | 411 Motor Speedway - Seymour, TN Tennessee State Champiohship Sportsmans, A Modifieds, Vintage Modifieds, Asphalt Mini Stock, Pro Late Model, Dirt Crate Late Models | Results | | Jesse Rupe (A Modifieds) | - | - | - | 7th |
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