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| 5/1/2021 | Florence Speedway - Walton, KY 35th Annual Ralph Latham Memorial Dirt Super Late Models: Lucas Oil Late Model Dirt Series DIRTcar UMP Modifieds: Summit American Modified Series Dirt Late Models, CRUSA Dirt Late Models | Results | | Jason Montgomery (DIRTcar UMP Modifieds) | 1st | - | - | 14th |
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| 5/30/2021 | Portsmouth Raceway Park - Portsmouth, OH CLETUS CLASSIC - MODIFIEDS $1,231 TO WIN & SALUTE THE TROOPS NIGHT by VALLERY FORD OF WAVERLY DIRTcar UMP Modifieds, Dirt Late Models, Economy Late Models, Limited Sport Mod | Results | | Jason Montgomery (DIRTcar UMP Modifieds) | 4th | - | - | 13th |
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| 7/2/2021 | Portsmouth Raceway Park - Portsmouth, OH Independence 50 Dirt Super Late Models: Lucas Oil Late Model Dirt Series DIRTcar UMP Modifieds, Economy Late Models, CRUSA Dirt Late Models | Results | | Jason Montgomery (DIRTcar UMP Modifieds) | 2nd | - | - | 9th |
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| 8/7/2021 | Portsmouth Raceway Park - Portsmouth, OH LEMLEY MOTORSPORTS Mod Squad Spectacular 3K to win Modifieds & MARY'S CLOTHESLINE BACK PACK GIVEAWAY DIRTcar UMP Modifieds, Dirt Late Models, Economy Late Models, Limited Sport Mod | Results | | Jason Montgomery (DIRTcar UMP Modifieds) | 4th | - | - | 9th |
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| 9/4/2021 | Portsmouth Raceway Park - Portsmouth, OH River Days Rumble - Presented by Pepsi Dirt Super Late Models: Lucas Oil Late Model Dirt Series DIRTcar UMP Modifieds, CRUSA Dirt Late Models, Limited Sport Mod | Results | | Jason Montgomery (DIRTcar UMP Modifieds) | 3rd | - | - | 5th |
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| 10/14/2021 | Portsmouth Raceway Park - Portsmouth, OH 41st ANNUAL DIRT TRACK WORLD CHAMPIONSHIP DIRTcar UMP Modifieds | Results | | Jason Montgomery (DIRTcar UMP Modifieds) | 4th | - | 1st | - |
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| 10/15/2021 | Portsmouth Raceway Park - Portsmouth, OH 41st Annual Dirt Track World Championship Dirt Super Late Models: Lucas Oil Late Model Dirt Series DIRTcar UMP Modifieds, Pro Legends, Economy Late Models, CRUSA Dirt Late Models | Results | | Jason Montgomery (DIRTcar UMP Modifieds) | - | - | - | - |
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| 10/16/2021 | Portsmouth Raceway Park - Portsmouth, OH 41st Annual Dirt Track World Championship Dirt Super Late Models: Lucas Oil Late Model Dirt Series DIRTcar UMP Modifieds, Pro Legends, Economy Late Models, CRUSA Dirt Late Models | Results | | Jason Montgomery (DIRTcar UMP Modifieds) | - | - | - | 18th |
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