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| 1/5/2023 | Talladega Short Track - Eastaboga, AL 2023 ICE BOWL Dirt Super Late Models, CRUSA Street Stocks, CRUSA Dirt Late Models, Sport Compact, Pure Stock, CRUSA Modified Sportsman, CRUSA Late Model Sportsman, Dirt Limited Late Models, Dirt Mini Stocks | Results | | Bobby Gregory (CRUSA Street Stocks) | - | - | - | - |
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| 1/6/2023 | Talladega Short Track - Eastaboga, AL 2023 ICE BOWL Dirt Super Late Models: American Late Model Iron-Man Series CRUSA Dirt Late Models: Crate Racin' USA Dirt Late Model Series CRUSA Street Stocks, Sport Compact, Pure Stock, CRUSA Modified Sportsman, CRUSA Late Model Sportsman, Dirt Limited Late Models, Dirt Mini Stocks | Results | | Bobby Gregory (CRUSA Street Stocks) | 7th | - | - | - |
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| 1/7/2023 | Talladega Short Track - Eastaboga, AL 2023 ICE BOWL Dirt Super Late Models: American Late Model Iron-Man Series CRUSA Dirt Late Models: Crate Racin' USA Dirt Late Model Series CRUSA Street Stocks, Sport Compact, Pure Stock, CRUSA Modified Sportsman, CRUSA Late Model Sportsman, Dirt Limited Late Models, Dirt Mini Stocks | Results | | Bobby Gregory (CRUSA Street Stocks) | - | - | 3rd | 19th |
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| 4/8/2023 | Camden Speedway - Camden, TN CRUSA Street Stocks, CRUSA Dirt Late Models, CRUSA Modified Sportsman, CRUSA Late Model Sportsman | Results | | Bobby Gregory (CRUSA Street Stocks) | - | - | - | 4th |
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| 4/15/2023 | Western Kentucky Speedway - Madisonville, KY Opening Night of Racing Factory Stocks, Hobby Stocks, Hornets, CRUSA Street Stocks | Results | | Bobby Gregory (CRUSA Street Stocks) | 2nd | - | - | 2nd |
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| 4/22/2023 | Tennessee National Raceway - Hohenwald, TN Outlaw Brawl Street Stocks, Vintage Modifieds, CRUSA Street Stocks, Pure Stock, Dirt 6-cyl Stock Cars, CRUSA Modified Sportsman, Dirt Limited Late Models, Dirt Mini Stocks | Results | | Bobby Gregory (CRUSA Street Stocks) | 6th | - | - | 12th |
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| 5/6/2023 | Western Kentucky Speedway - Madisonville, KY 3rd Annual Spring Fling Factory Stocks, Hobby Stocks, B Modifieds, Hornets, CRUSA Street Stocks | Results | | Bobby Gregory (CRUSA Street Stocks) | 5th | - | - | 8th |
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| 5/14/2023 | Windy Hollow Speedway - Owensboro, KY OPENING NIGHT/ MOTHERS DAY SPECIAL $600 TO WIN Hobby Stocks, Stock Cars, B Modifieds, Hornets, CRUSA Street Stocks, Pure Stock | Results | | Bobby Gregory (Street Stocks) | - | - | - | - | | Bobby Gregory (CRUSA Street Stocks) | 2nd | - | - | 3rd |
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| 5/26/2023 | Paducah International Raceway - Paducah, KY DIRTcar UMP Modifieds, DIRTcar Sport Compact, Factory Stocks, Stock Cars, Street Stocks, CRUSA Street Stocks, Mod Lites, 602 Crate Late Models | Results | | Bobby Gregory (CRUSA Street Stocks) | 4th | - | - | 9th |
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| 5/27/2023 | Western Kentucky Speedway - Madisonville, KY Kentucky Top Dog Street Stock Series Factory Stocks, Hobby Stocks, Street Stocks, Hornets, CRUSA Street Stocks | Results | | Bobby Gregory (CRUSA Street Stocks) | 2nd | - | - | 25th |
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| 5/28/2023 | Windy Hollow Speedway - Owensboro, KY TOP DOG STREET DOG SPECIAL -- $2000 TO WIN Hobby Stocks, Stock Cars, Hornets, CRUSA Street Stocks, Pure Stock, Dirt Crate Late Models | Results | | Bobby Gregory (CRUSA Street Stocks) | 1st | - | - | 2nd |
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| 6/4/2023 | Windy Hollow Speedway - Owensboro, KY BATTLE OF THE HORNETS $2500 TO WIN MINI STOCKS Hobby Stocks, Stock Cars, B Modifieds, Hornets, CRUSA Street Stocks, Pure Stock | Results | | Bobby Gregory (CRUSA Street Stocks) | 1st | - | - | 1st |
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| 6/10/2023 | Western Kentucky Speedway - Madisonville, KY Dustin Ray Memorial Factory Stocks, Hobby Stocks, Hornets, CRUSA Street Stocks | Results | | Bobby Gregory (Hobby Stocks) | - | - | - | 1st |
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| 6/18/2023 | Windy Hollow Speedway - Owensboro, KY KING OF THE RUSTY BOLTS -- $700 TO WIN Hobby Stocks, Stock Cars, Hornets, Pony Stock, CRUSA Street Stocks, Pure Stock, Dirt Crate Late Models | Results | | Bobby Gregory (CRUSA Street Stocks) | 1st | - | - | 1st |
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| 6/23/2023 | Western Kentucky Speedway - Madisonville, KY 5th Annual King of the Bluegrass CRUSA Street Stocks: Ultimate Street Stock Challenge Factory Stocks, Hobby Stocks, Hornets | Results | | Bobby Gregory (Factory Stocks) | - | - | - | 1st | | Bobby Gregory (CRUSA Street Stocks) | 7th | - | - | - |
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| 6/24/2023 | Western Kentucky Speedway - Madisonville, KY 5th Annual King of the Bluegrass CRUSA Street Stocks: Ultimate Street Stock Challenge Factory Stocks, Hobby Stocks, Hornets | Results | | Bobby Gregory (Factory Stocks) | 1st | - | - | 1st | | Bobby Gregory (Hobby Stocks) | 8th | - | - | 2nd | | Bobby Gregory (CRUSA Street Stocks) | - | - | 4th | - |
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| 7/8/2023 | Western Kentucky Speedway - Madisonville, KY $1000 to win UMP Mods DIRTcar UMP Modifieds, Factory Stocks, Hobby Stocks, Hornets, CRUSA Street Stocks | Results | | Bobby Gregory (CRUSA Street Stocks) | - | - | - | 4th |
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| 7/16/2023 | Windy Hollow Speedway - Owensboro, KY SUMMER SIZZLER -- Hobby Stocks, Stock Cars, B Modifieds, Hornets, Pony Stock, CRUSA Street Stocks, Pure Stock | Results | | Bobby Gregory (CRUSA Street Stocks) | 5th | - | - | 9th |
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| 7/22/2023 | Western Kentucky Speedway - Madisonville, KY $1000 to win UMP Modifieds plus all regular classes DIRTcar UMP Modifieds, Factory Stocks, Hobby Stocks, Hornets, CRUSA Street Stocks | Results | | Bobby Gregory (CRUSA Street Stocks) | 2nd | - | - | 1st |
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| 7/28/2023 | Paducah International Raceway - Paducah, KY Bombers Beat Down DIRTcar UMP Modifieds, DIRTcar Sport Compact, Factory Stocks, Stock Cars, Hornets, CRUSA Street Stocks, Mod Lites, 602 Crate Late Models | Results | | Bobby Gregory (Factory Stocks) | 2nd | - | - | 2nd | | Bobby Gregory (Stock Cars) | 1st | - | - | 1st |
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| 7/30/2023 | Windy Hollow Speedway - Owensboro, KY KING OF THE BOMBERS -- $1000 TO WIN -- E-Z AUTO PARTS & SALES SPECIAL Hobby Stocks, Stock Cars, Hornets, CRUSA Street Stocks, Pure Stock, Dirt Crate Late Models | Results | | Bobby Gregory (CRUSA Street Stocks) | 1st | - | - | 5th |
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| 8/12/2023 | Western Kentucky Speedway - Madisonville, KY Rusty Bolt Rumble Factory Stocks, Hobby Stocks, Hornets, CRUSA Street Stocks | Results | | Bobby Gregory (CRUSA Street Stocks) | 2nd | - | - | 5th |
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| 8/20/2023 | Windy Hollow Speedway - Owensboro, KY KING OF THE CRATES --- $1000 TO WIN Hobby Stocks, Stock Cars, Hornets, Pony Stock, CRUSA Street Stocks, Pure Stock, Dirt Crate Late Models | Results | | Bobby Gregory (CRUSA Street Stocks) | 3rd | - | - | 4th |
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| 9/3/2023 | Windy Hollow Speedway - Owensboro, KY KING OF THE ECONOMIES -- $500 TO WIN Hobby Stocks, Stock Cars, B Modifieds, Hornets, CRUSA Street Stocks, Pure Stock | Results | | Bobby Gregory (CRUSA Street Stocks) | 2nd | - | - | 3rd |
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| 9/9/2023 | Thunderhill Raceway - Summertown, TN Melissa Cothran Memorial Race Dirt Late Models, Dwarf, Pony Stock, CRUSA Street Stocks, Outlaw Hobby Stocks, CRUSA Modified Sportsman, CRUSA Late Model Sportsman, Speedstr, Asphalt Bombers | Results | | Bobby Gregory (Asphalt Bombers) | 1st | - | - | 13th |
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| 9/17/2023 | Windy Hollow Speedway - Owensboro, KY SCRAPPER YOUNG GUNS SPECIAL -- $250 TO WIN Hobby Stocks, Stock Cars, Hornets, Pony Stock, CRUSA Street Stocks, Pure Stock, Dirt Crate Late Models | Results | | Bobby Gregory (CRUSA Street Stocks) | 1st | - | - | 2nd |
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| 9/23/2023 | Western Kentucky Speedway - Madisonville, KY $1000 to win Mini Stock Factory Stocks, Hobby Stocks, Hornets, CRUSA Street Stocks | Results | | Bobby Gregory (CRUSA Street Stocks) | 3rd | - | - | 4th |
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| 10/1/2023 | Windy Hollow Speedway - Owensboro, KY RACE ON MEMORIAL -- $668.08 TO WIN ALL CLASSES Hobby Stocks, Stock Cars, Hornets, CRUSA Street Stocks, Pure Stock, Dirt Crate Late Models | Results | | Bobby Gregory (CRUSA Street Stocks) | 1st | - | - | 5th |
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| 10/14/2023 | Western Kentucky Speedway - Madisonville, KY $2000 to win CRUSA Street Stock Factory Stocks, Hobby Stocks, Hornets, CRUSA Street Stocks | Results | | Bobby Gregory (Hobby Stocks) | 1st | - | - | 15th | | Bobby Gregory (CRUSA Street Stocks) | 6th | - | - | 8th |
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| 10/15/2023 | Windy Hollow Speedway - Owensboro, KY CHAMPIONSHIP NIGHT -- LAST POINTS RACE Hobby Stocks, Stock Cars, Hornets, CRUSA Street Stocks, Pure Stock, Dirt Crate Late Models | Results | | Bobby Gregory (Stock Cars) | 5th | - | - | DNS | | Bobby Gregory (CRUSA Street Stocks) | 3rd | - | - | 3rd |
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| 10/21/2023 | Western Kentucky Speedway - Madisonville, KY Fall Classic Factory Stocks, Hobby Stocks, Hornets, CRUSA Street Stocks | Results | | Bobby Gregory (Hobby Stocks) | 1st | - | - | 1st | | Bobby Gregory (CRUSA Street Stocks) | 1st | - | - | 1st |
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| 10/28/2023 | Thunderhill Raceway - Summertown, TN Keota Street Stock Race Factory Stocks, CRUSA Street Stocks, Outlaw Hobby Stocks, CRUSA Late Model Sportsman, Speedstr, Asphalt Bombers | Results | | Bobby Gregory (CRUSA Street Stocks) | 6th | - | 2nd | 14th |
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| 11/18/2023 | Duck River Raceway Park - Shelbyville, TN The Gobbler $10K to win Super Late Models with $3K to win enduro Dirt Super Late Models: Hunt The Front Super Dirt Series Dwarf, Hornets, Enduro, Pony Stock, Pure Stock, CRUSA Modified Sportsman, 602 Crate Late Models | Results | | Bobby Gregory (Enduro) | - | - | - | 50th |
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