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| 1/4/2020 | Talladega Short Track - Eastaboga, AL 29th 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 Super Dirt Late Models, CRUSA Late Model Sportsman | Results | | Chad Winkles (CRUSA Street Stocks) | 1st | - | - | - |
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| 1/5/2020 | Talladega Short Track - Eastaboga, AL 29th 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 Super Dirt Late Models, CRUSA Late Model Sportsman | Results | | Chad Winkles (CRUSA Street Stocks) | - | - | - | 3rd |
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| 5/16/2020 | Thunderhill Raceway - Summertown, TN Season Opener Dirt Late Models, Hornets, Pony Stock, CRUSA Street Stocks, CRUSA Dirt Late Models, Outlaw Hobby Stocks, CRUSA Modified Sportsman, Mod Lites, Speedstr | Results | | Chad Winkles (CRUSA Street Stocks) | 3rd | - | - | 5th |
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| 5/23/2020 | Thunderhill Raceway - Summertown, TN SAS $5,000 To Win Dirt Super Late Models, Dirt Late Models, Hornets, Pony Stock, CRUSA Street Stocks, CRUSA Dirt Late Models, Outlaw Hobby Stocks, CRUSA Modified Sportsman, Mod Lites, Speedstr | Results | | Chad Winkles (CRUSA Street Stocks) | 2nd | - | 1st | - |
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| 7/4/2020 | Thunderhill Raceway - Summertown, TN Weekly Race Event Dirt Super Late Models, Hornets, Pony Stock, CRUSA Street Stocks, CRUSA Dirt Late Models, Outlaw Hobby Stocks, CRUSA Modified Sportsman, Mod Lites, Speedstr | Rain Out |
| 7/11/2020 | Thunderhill Raceway - Summertown, TN Weekly Race Event Dirt Late Models, Hornets, Pony Stock, CRUSA Street Stocks, CRUSA Dirt Late Models, Pure Stock, Outlaw Hobby Stocks, CRUSA Modified Sportsman, Mod Lites, Speedstr | Results | | Chad Winkles (CRUSA Street Stocks) | 3rd | - | - | 1st |
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| 8/12/2020 | Whynot Motorsports Park - Meridian, MS Practice Night Hobby Stocks: Dirts4Racing Street Stocks | Results | | Chad Winkles (Hobby Stocks) | - | - | - | - |
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| 8/13/2020 | Whynot Motorsports Park - Meridian, MS Night 1 Qualifiers Hobby Stocks: Dirts4Racing Street Stocks | Results | | Chad Winkles (Hobby Stocks) | - | - | - | - |
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| 8/14/2020 | Whynot Motorsports Park - Meridian, MS Night 2 Qualifiers and Alphabet Soup Elimination Features Hobby Stocks: Dirts4Racing Street Stocks | Results | | Chad Winkles (Hobby Stocks) | - | 9th | - | - |
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| 8/15/2020 | Whynot Motorsports Park - Meridian, MS Night 3- Feature Events Hobby Stocks: Dirts4Racing Street Stocks | Results | | Chad Winkles (Hobby Stocks) | - | - | - | 26th |
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| 9/5/2020 | Thunderhill Raceway - Summertown, TN Weekly Race Event Dirt Late Models, Hornets, Pony Stock, CRUSA Street Stocks, CRUSA Dirt Late Models, Outlaw Hobby Stocks, CRUSA Modified Sportsman, Mod Lites, Speedstr | Results | | Chad Winkles (CRUSA Street Stocks) | 8th | - | - | DNS |
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