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| 1/7/2021 | Talladega Short Track - Eastaboga, AL 30th 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 Late Model Sportsman | Results | | Drew Kennedy (CRUSA Dirt Late Models) | - | - | - | - |
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| 1/8/2021 | Talladega Short Track - Eastaboga, AL 30th Annual ICE BOWL Practice 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 Late Model Sportsman | Results | | Drew Kennedy (CRUSA Dirt Late Models) | - | - | - | - |
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| 1/9/2021 | Talladega Short Track - Eastaboga, AL 30th Annual ICE BOWL Qualifying and Heat Races 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 Late Model Sportsman | Results | | Drew Kennedy (CRUSA Dirt Late Models) | 6th | - | - | - |
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| 1/10/2021 | Talladega Short Track - Eastaboga, AL 30th Annual ICE BOWL B-Mains and Feature CRUSA Dirt Late Models: Crate Racin' USA Dirt Late Model Series Dirt Super Late Models, Dirt Late Models, CRUSA Street Stocks, CRUSA Modified Sportsman, CRUSA Late Model Sportsman | Results | | Drew Kennedy (CRUSA Dirt Late Models) | - | - | 1st | 12th |
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| 1/13/2021 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Sunshine Nationals - Practice Night Dirt Super Late Models: World of Outlaws - Late Models CRUSA Dirt Late Models: Crate Racin' USA Dirt Late Model Series Dirt Late Models, Dirt Crate Late Models | Results | | Drew Kennedy (CRUSA Dirt Late Models) | - | - | - | - |
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| 1/14/2021 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Sunshine Nationals - Night #1 Dirt Super Late Models: World of Outlaws - Late Models CRUSA Dirt Late Models: Crate Racin' USA Dirt Late Model Series Dirt Late Models, Dirt Crate Late Models | Results | | Drew Kennedy (CRUSA Dirt Late Models) | 5th | - | 3rd | - |
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| 1/15/2021 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Sunshine Nationals - Night #2 Dirt Super Late Models: World of Outlaws - Late Models CRUSA Dirt Late Models: Crate Racin' USA Dirt Late Model Series Dirt Late Models, Dirt Crate Late Models | Rain Out |
| 1/16/2021 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Sunshine Nationals - Night #3 Dirt Super Late Models: World of Outlaws - Late Models CRUSA Dirt Late Models: Crate Racin' USA Dirt Late Model Series Dirt Late Models, Dirt Crate Late Models | Results | | Drew Kennedy (CRUSA Dirt Late Models) | 5th | - | 3rd | 19th |
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| 2/4/2021 | East Bay Raceway Park - Tampa, FL East Bay Winter Nationals CRUSA Dirt Late Models: Crate Racin' USA Dirt Late Model Series | Results | | Drew Kennedy (CRUSA Dirt Late Models) | 2nd | - | - | 15th |
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| 2/5/2021 | East Bay Raceway Park - Tampa, FL East Bay Winter Nationals CRUSA Dirt Late Models: Crate Racin' USA Dirt Late Model Series Dirt Super Late Models | Results | | Drew Kennedy (CRUSA Dirt Late Models) | 2nd | - | - | 13th |
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| 2/6/2021 | East Bay Raceway Park - Tampa, FL East Bay Winter Nationals CRUSA Dirt Late Models: Crate Racin' USA Dirt Late Model Series Dirt Super Late Models | Results | | Drew Kennedy (CRUSA Dirt Late Models) | 8th | - | 10th | 14th |
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| 6/4/2021 | Wartburg Speedway - Wartburg, TN Dirt Super Late Models: Iron-Man Late Model Series | Results | | Drew Kennedy (Dirt Super Late Models) | - | - | - | 9th |
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| 9/18/2021 | Lake Cumberland Speedway - Somerset, KY Mod Mania Dirt Super Late Models: Iron-Man Late Model Series A Modifieds: Iron-Man Modified Series | Results | | Drew Kennedy (Dirt Super Late Models) | - | - | - | 7th |
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| 10/16/2021 | Mountain View Raceway - Spring City, TN Championship Night Midgets, Hobby Stocks, Sportsmans, Street Stocks, Dirt Late Models, Economy Late Models, Pure Stock, Dirt Big Block Modifieds, Ladies - Pure Stocks | Results | | Drew Kennedy (Dirt Late Models) | - | - | - | 17th |
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