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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 | | Oakley Gillespie (CRUSA Modified Sportsman) | - | - | - | - |
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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 | | Oakley Gillespie (CRUSA Modified Sportsman) | - | - | - | - |
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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 | | Oakley Gillespie (CRUSA Modified Sportsman) | 3rd | - | - | - |
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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 | | Oakley Gillespie (CRUSA Modified Sportsman) | - | - | - | 6th |
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| 7/31/2021 | Thunderhill Raceway - Summertown, TN King of the Hill CRUSA Dirt Late Models: Crate Racin' USA Dirt Late Model Series Hornets, Pony Stock, CRUSA Street Stocks, Pure Stock, Outlaw Hobby Stocks, CRUSA Modified Sportsman, Speedstr | Results | | Oakley Gillespie (CRUSA Dirt Late Models) | - | - | 1st | 10th |
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| 8/27/2021 | North Alabama Speedway - Tuscumbia, AL King of Crate - Night #1 CRUSA Dirt Late Models: Crate Racin' USA Dirt Late Model Series | Results | | Oakley Gillespie (CRUSA Dirt Late Models) | 5th | - | - | - |
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| 8/28/2021 | North Alabama Speedway - Tuscumbia, AL King of Crate - Night #2 CRUSA Dirt Late Models: Crate Racin' USA Dirt Late Model Series | Results | | Oakley Gillespie (CRUSA Dirt Late Models) | - | - | - | 17th |
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| 10/1/2021 | Talladega Short Track - Eastaboga, AL NASCAR Weekend #2 - 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 | | Oakley Gillespie (CRUSA Dirt Late Models) | - | - | - | 20th |
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| 10/2/2021 | Talladega Short Track - Eastaboga, AL NASCAR Weekend #2 - Night #2 CRUSA Dirt Late Models: Crate Racin' USA Dirt Late Model Series Dirt Super Late Models, Sport Compact, Pure Stock, CRUSA Modified Sportsman, CRUSA Late Model Sportsman | Results | | Oakley Gillespie (CRUSA Dirt Late Models) | 3rd | - | - | 20th |
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| 11/27/2021 | Thunderhill Raceway - Summertown, TN Turkey Bash Mod Lites: United CC Modified Series Enduro, Pony Stock, CRUSA Street Stocks, CRUSA Dirt Late Models, Pure Stock, Outlaw Hobby Stocks, CRUSA Modified Sportsman, Speedstr | Results | | Oakley Gillespie (CRUSA Dirt Late Models) | - | - | - | 1st |
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