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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 | | Mason Ashby (Hornets) | 6th | - | - | 12th |
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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 | | Mason Ashby (Hornets) | 1st | - | - | 2nd |
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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 | | Mason Ashby (Hornets) | 1st | - | - | 3rd |
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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 | | Mason Ashby (Hornets) | 3rd | - | - | 8th |
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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 | | Mason Ashby (Hornets) | 1st | - | - | 11th |
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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 | | Mason Ashby (Hornets) | 4th | - | - | 18th |
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| 9/3/2021 | Windy Hollow Speedway - Owensboro, KY FRI SPECIAL! Mini Stock, Bombers plus 602 Late Models and B-Mods! B Modifieds, Hornets, Pure Stock, Dirt Crate Late Models | Results | | Mason Ashby (Hornets) | 5th | - | - | 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 | | Mason Ashby (Hornets) | 3rd | - | - | 5th |
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| 9/26/2021 | Windy Hollow Speedway - Owensboro, KY 51st Birthday Party! Twins to WIN - each class double features! Double Features, Double Money! Hobby Stocks, Stock Cars, Street Stocks, Hornets, Pony Stock, Pure Stock, Dirt Crate Late Models | Results | | Mason Ashby (Hornets) | 9th | - | - | 4th |
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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 | | Mason Ashby (Hornets) | 3rd | - | - | 4th |
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| 11/28/2021 | Windy Hollow Speedway - Owensboro, KY 1st Annual Gobblers 50's DIRTcar Factory Stock, Hornets, Pony Stock, Pure Stock | Results | | Mason Ashby (Hornets) | - | - | - | 8th |
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