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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 | | Jason Wooldridge (Pony Stock) | 4th | - | - | 3rd |
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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 | | Jason Wooldridge (Pony Stock) | 7th | - | - | 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 | | Jason Wooldridge (Pony Stock) | 1st | - | - | 3rd |
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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 | | Jason Wooldridge (Pony Stock) | 5th | - | - | 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 | | Jason Wooldridge (Pony Stock) | 3rd | - | - | 4th |
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