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| 5/16/2021 | Windy Hollow Speedway - Owensboro, KY Sunday Sunday Sunday! $1,000 Street Stock WIN Hobby Stocks, Stock Cars, Street Stocks, Hornets, Pony Stock, Pure Stock | Results | | Jeremy Brown (Hobby Stocks) | DNS | - | - | DNS | | Jeremy Brown (Street Stocks) | 6th | - | - | DNS |
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| 5/23/2021 | Windy Hollow Speedway - Owensboro, KY Little Scrapper Kid's Club Night! $1 admission for kids 8-12! All Classes racing Hobby Stocks, Stock Cars, Street Stocks, Hornets, Pony Stock, Pure Stock | Results | | Jeremy Brown (Hobby Stocks) | 3rd | - | - | 4th |
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| 6/5/2021 | Western Kentucky Speedway - Madisonville, KY Tribute to "Little" John Gray featuring 3rd Annual King of the Street Stocks Factory Stocks, Hobby Stocks, Street Stocks, Hornets | Results | | Jeremy Brown (Street Stocks) | DNS | - | DNS | - |
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| 6/13/2021 | Windy Hollow Speedway - Owensboro, KY Cruiser Night! JKV $500 bonus for winner! All classes Hobby Stocks, Stock Cars, Street Stocks, Hornets, Pony Stock, Pure Stock | Results | | Jeremy Brown (Hobby Stocks) | 5th | - | - | 1st |
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| 6/20/2021 | Windy Hollow Speedway - Owensboro, KY King of the Hollow! $1,000 win in 5 classes, $300 win Scrappers Hobby Stocks, Stock Cars, Street Stocks, Hornets, Pony Stock, Pure Stock | Results | | Jeremy Brown (Hobby Stocks) | 3rd | - | - | DNS |
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| 6/27/2021 | Windy Hollow Speedway - Owensboro, KY Bomber Powder Puff! Plus all classes! Hobby Stocks, Stock Cars, B Modifieds, Street Stocks, Hornets, Pure Stock | Results | | Jeremy Brown (Hobby Stocks) | 2nd | - | - | 1st |
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| 7/25/2021 | Windy Hollow Speedway - Owensboro, KY Mini Stock Night! $500 bonus from JKV for winner! Hobby Stocks, Stock Cars, Street Stocks, Hornets, Pony Stock, Pure Stock | Results | | Jeremy Brown (Hobby Stocks) | DNS | - | - | 5th |
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| 8/1/2021 | Windy Hollow Speedway - Owensboro, KY Legend's of Windy Hollow Night! Class of 2021 Honored! All classes racing and Bonus $$ for winners! Hobby Stocks, Stock Cars, Street Stocks, Hornets, Pony Stock, Pure Stock | Results | | Jeremy Brown (Hobby Stocks) | 3rd | - | - | 2nd |
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| 8/8/2021 | Windy Hollow Speedway - Owensboro, KY Little Scrappers and Scrappers Bonus Night! $500 bonus to winner from JKV Core Hobby Stocks, Stock Cars, Street Stocks, Hornets, Pony Stock, Pure Stock | Results | | Jeremy Brown (Hobby Stocks) | 2nd | - | - | 2nd |
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| 8/15/2021 | Windy Hollow Speedway - Owensboro, KY UMP Open Wheel Modifieds! DIRTcar UMP Modifieds, Hobby Stocks, Stock Cars, Street Stocks, Hornets, Pony Stock, Pure Stock | Results | | Jeremy Brown (Hobby Stocks) | 3rd | - | - | DNS |
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| 8/29/2021 | Windy Hollow Speedway - Owensboro, KY UMP Mini Stocks --- JKV Core and Auto Recycling --- $1000 To Win --- $500 Bonus for Bomber Hobby Stocks, Stock Cars, Street Stocks, Hornets, Pony Stock, Pure Stock | Results | | Jeremy Brown (Hobby Stocks) | 4th | - | - | 3rd |
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| 9/12/2021 | Windy Hollow Speedway - Owensboro, KY Rusty Bolt Night! JKV $500 bonus for winner! All classes Hobby Stocks, Stock Cars, Street Stocks, Hornets, Pony Stock, Pure Stock | Results | | Jeremy Brown (Hobby Stocks) | 1st | - | - | 1st |
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| 10/17/2021 | Windy Hollow Speedway - Owensboro, KY SEASON FINALE! RACE ON plus Enduro and Fun Day! PLUS Halloween and track or treat! DIRTcar Factory Stock, Hobby Stocks, Stock Cars, Street Stocks, Hornets, Pony Stock, Sport Compact, Pure Stock, Figure 8 - RWD-Open | Results | | Jeremy Brown (Hobby Stocks) | 2nd | - | - | 5th |
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