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| 3/6/2021 | Smoky Mountain Speedway - Maryville, TN 8th Annual Tennessee Tipoff Dirt Super Late Models: World of Outlaws - Late Models Dirt Late Models, Hornets, CRUSA Dirt Late Models | Results | | Jake Whitehead (Dirt Late Models) | - | - | - | 13th |
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| 4/17/2021 | Smoky Mountain Speedway - Maryville, TN Rockin' With The Stars Dirt Super Late Models, Sportsmans, Sport Compact, Dirt Crate Late Models | Results | | Jake Whitehead (Sportsmans) | - | - | - | 1st |
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| 5/14/2021 | 411 Motor Speedway - Seymour, TN Weekly Racing Dirt Super Late Models, Sportsmans, A Modifieds, Vintage Modifieds, Economy Late Models, Asphalt Mini Stock, Dirt Crate Late Models | Results | | Jake Whitehead (Asphalt Mini Stock) | - | - | - | - | | Jake Whitehead (Dirt Crate Late Models) | - | - | - | 10th |
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| 5/15/2021 | I-75 Raceway - Sweetwater, TN UCRA Spring Loaded 40 Plus Local Classes Factory Stocks, Asphalt Mini Stocks, Hobby Stocks, Economy Late Models, Asphalt 4-Cylinders, Asphalt Rookie Stocks, Pro Late Model, Dirt Limited Late Models | Results | | Jake Whitehead (Pro Late Model) | 4th | - | - | 7th |
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| 5/29/2021 | Smoky Mountain Speedway - Maryville, TN Memorial Day Mayhem In The Mountains Sportsmans, Sport Compact, Dirt Crate Late Models, 604 Crate Late Models | Results | | Jake Whitehead (Sportsmans) | - | - | - | 1st |
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| 5/31/2021 | 411 Motor Speedway - Seymour, TN Scott Sexton Memorial Valvoline Iron Man Series Dirt Super Late Models: Iron-Man Late Model Series Sportsmans, A Modifieds, Street Stocks, Vintage Modifieds, CRUSA Dirt Late Models, Dirt Crate Late Models | Results | | Jake Whitehead (Dirt Crate Late Models) | - | - | - | 21st |
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| 6/25/2021 | 411 Motor Speedway - Seymour, TN The 10th Annual JT Kerr Memorial - Day 1 Sportsmans, A Modifieds, Street Stocks, Vintage Modifieds, Economy Late Models, Dirt Crate Late Models | Results | | Jake Whitehead (Dirt Crate Late Models) | 7th (DNF) | - | - | - |
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| 6/26/2021 | 411 Motor Speedway - Seymour, TN The 10th Annual JT Kerr Memorial - Day 2 Hobby Stocks, Sportsmans, A Modifieds, Economy Late Models, Asphalt Mini Stock, Dirt Crate Late Models | Results | | Jake Whitehead (Economy Late Models) | - | - | - | 8th | | Jake Whitehead (Dirt Crate Late Models) | 7th | - | - | - |
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| 7/10/2021 | Smoky Mountain Speedway - Maryville, TN Mountain Moonshine Classic Dirt Super Late Models: Lucas Oil Late Model Dirt Series Economy Late Models, Dirt Crate Late Models | Postponed |
| 7/20/2021 | I-75 Raceway - Sweetwater, TN Dirt Super Late Models: Schaeffer's Southern Nationals Series Hobby Stocks, Economy Late Models, Asphalt 4-Cylinders, Asphalt Rookie Stocks | Results | | Jake Whitehead (Economy Late Models) | - | - | - | 1st |
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| 7/24/2021 | I-75 Raceway - Sweetwater, TN UCRA + Weekly Divisions Factory Stocks, Asphalt Mini Stocks, Hobby Stocks, Super Sports, Dirt Late Models, Economy Late Models, Asphalt 4-Cylinders, Asphalt Rookie Stocks | Results | | Jake Whitehead (Economy Late Models) | - | - | - | 4th |
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| 8/7/2021 | Smoky Mountain Speedway - Maryville, TN Smoky Mountain Summer Showdown Sportsmans, Dirt Late Models, Sport Compact, 604 Crate Late Models | Results | | Jake Whitehead (Sportsmans) | - | - | - | 1st |
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| 8/14/2021 | 411 Motor Speedway - Seymour, TN Area 51 Open Wheel Modifieds Day 2 Hobby Stocks, Sportsmans, A Modifieds, Economy Late Models, Asphalt Mini Stock, Dirt Crate Late Models | Rain Out |
| 9/25/2021 | Smoky Mountain Speedway - Maryville, TN King Of The Mountain Fall Classic Dirt Super Late Models, Dirt Late Models, Sport Compact | Results | | Jake Whitehead (Dirt Late Models) | - | - | - | 11th |
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| 10/16/2021 | Smoky Mountain Speedway - Maryville, TN Tennessee State Championship Sportsmans, Sport Compact, 604 Crate Late Models | Results | | Jake Whitehead (Sportsmans) | - | - | - | 1st |
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