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| 1/4/2020 | Talladega Short Track - Eastaboga, AL 29th Annual Ice Bowl CRUSA Dirt Late Models: Crate Racin' USA Dirt Late Model Series Dirt Super Late Models, Dirt Late Models, CRUSA Street Stocks, Sport Compact, Pure Stock, CRUSA Modified Sportsman, CRUSA Super Dirt Late Models, CRUSA Late Model Sportsman | Results | | Oliver Gentry (Dirt Super Late Models) | 1st | - | - | 1st |
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| 1/5/2020 | Talladega Short Track - Eastaboga, AL 29th Annual Ice Bowl CRUSA Dirt Late Models: Crate Racin' USA Dirt Late Model Series Dirt Super Late Models, Dirt Late Models, CRUSA Street Stocks, Sport Compact, Pure Stock, CRUSA Modified Sportsman, CRUSA Super Dirt Late Models, CRUSA Late Model Sportsman | Results | | Oliver Gentry (Dirt Super Late Models) | - | - | - | 1st |
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| 5/2/2020 | Boyd's Speedway - Ringgold, GA 2020 DIRT SHOW DOWN EVENT SUPER LATE MODELS $5000 AND MORE Dirt Super Late Models, DIRTcar Late Models, Dirt Late Models, Economy Late Models | Results | | Oliver Gentry (Dirt Super Late Models) | - | - | - | - |
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| 6/19/2020 | Talladega Short Track - Eastaboga, AL Nascar Weekend Friday Night Dirt Super Late Models, Dirt Late Models, CRUSA Dirt Late Models, Sport Compact, Pure Stock, CRUSA Modified Sportsman, CRUSA Late Model Sportsman | Results | | Oliver Gentry (CRUSA Dirt Late Models) | 3rd | - | - | 7th |
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| 9/26/2020 | Talladega Short Track - Eastaboga, AL Dirt Super Late Models, Dirt Late Models, CRUSA Dirt Late Models, Sport Compact, Pure Stock, CRUSA Modified Sportsman, CRUSA Late Model Sportsman | Results | | Oliver Gentry (Dirt Late Models) | - | - | - | 4th |
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| 10/2/2020 | Talladega Short Track - Eastaboga, AL NASCAR Weekend - Night #1 CRUSA Dirt Late Models: Crate Racin' USA Dirt Late Model Series Dirt Super Late Models, Dirt Late Models, Sport Compact, Pure Stock, CRUSA Modified Sportsman, CRUSA Late Model Sportsman | Results | | Oliver Gentry (Dirt Late Models) | - | - | - | 9th |
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| 10/3/2020 | Talladega Short Track - Eastaboga, AL NASCAR Weekend - Night #2 CRUSA Dirt Late Models: Crate Racin' USA Dirt Late Model Series Dirt Super Late Models, Dirt Late Models, Sport Compact, Pure Stock, CRUSA Modified Sportsman, CRUSA Late Model Sportsman | Results | | Oliver Gentry (Dirt Late Models) | - | - | - | 8th |
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| 10/30/2020 | Boyd's Speedway - Ringgold, GA TOPLESS OUTLAWS LATE MODELS $2500 TO WIN Asphalt Super Late Models, Dirt Super Late Models, Street Stocks, Dirt Late Models, Economy Late Models, CRUSA Dirt Late Models | Results | | Oliver Gentry (CRUSA Dirt Late Models) | - | - | - | 9th |
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