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| 4/8/2023 | Warren County Speedway - Indianola, IA SEASON OPENER! - Sponsored by Southtown Dodge & Jeep Factory Stocks, Hobby Stocks, Stock Cars, Winged A-Class, Street Stocks, Hornets, Dirt Pro Trucks, Sport Compact | Results | | Jackson Gray (Winged A-Class) | 2nd | - | - | DNS |
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| 4/28/2023 | Brooklyn Raceway - Brooklyn, IA Spring Nationals Hobby Stocks, Stock Cars, Winged A-Class, Junior Sprints, Dirt Pro Trucks, Sport Compact, IMCA Sport Compact, DIRTcar 4 Cylinders, Figure 8 - FWD Stock, Figure 8 - RWD-Stock, Figure 8 - RWD-Open | Results | | Jackson Gray (Winged A-Class) | 2nd | - | - | 2nd |
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| 4/29/2023 | Sweet Springs Motorsports Complex - Sweet Springs, MO Restricted 'A' Class: NOW600 Restricted Micros Winged A-Class: NOW600 A-Class Micros Stock Non-Wing: NOW600 Non-Wing Micros Junior Sprints | Results | | Jackson Gray (Winged A-Class) | 3rd | - | - | 12th |
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| 5/6/2023 | Jefferson County Speedway - Fairbury, NE JayHusker Micros plus Sport Compacts Restricted 'A' Class: NOW600 Restricted Micros Winged A-Class: NOW600 A-Class Micros Stock Non-Wing: NOW600 Non-Wing Micros Dirt Mini Trucks, Junior Sprints, 600cc Modifieds, Sportsman Micros, Sport Compact | Results | | Jackson Gray (Winged A-Class) | 8th | - | - | - |
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| 5/19/2023 | Brooklyn Raceway - Brooklyn, IA Marvin Housley Memorial Race Hobby Stocks, Winged A-Class, Junior Sprints, Dirt Pro Trucks, Sport Compact, IMCA Sport Compact, DIRTcar 4 Cylinders, Figure 8 - FWD Stock, Figure 8 - RWD-Stock, Figure 8 - RWD-Open | Results | | Jackson Gray (Winged A-Class) | 1st | - | - | 6th (DNF) |
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| 5/26/2023 | KAM Raceway - Hastings, NE Memorial Day Weekend - Day 1 Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Dirt Cage Kart Junior 1, Dirt Cage Kart Junior 2, Flat Adult Clone, Flat Jr. 1 Clone Heavy | Results | | Jackson Gray (Winged A-Class) | 5th | - | - | 11th |
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| 5/27/2023 | Warren County Speedway - Indianola, IA 2023 WC Race #4 Factory Stocks, Hobby Stocks, Stock Cars, Winged A-Class, Street Stocks, Hornets, Dirt Pro Trucks, Sport Compact | Results | | Jackson Gray (Winged A-Class) | 3rd | - | - | 2nd |
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| 5/28/2023 | Brooklyn Raceway - Brooklyn, IA Brooklyn Races Hobby Stocks, Stock Cars, Winged A-Class, Junior Sprints, Dirt Pro Trucks, IMCA Sport Compact, DIRTcar 4 Cylinders, Figure 8 - FWD Stock, Figure 8 - RWD-Stock, Figure 8 - RWD-Open | Results | | Jackson Gray (Winged A-Class) | 2nd | - | - | 3rd |
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| 6/3/2023 | Warren County Speedway - Indianola, IA 2023 WC Race #5 Factory Stocks, Hobby Stocks, Stock Cars, Winged A-Class, Street Stocks, Hornets, Dirt Pro Trucks, Sport Compact | Results | | Jackson Gray (Winged A-Class) | 1st | - | - | 1st |
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| 6/9/2023 | Brooklyn Raceway - Brooklyn, IA Brooklyn Races Hobby Stocks, Winged A-Class, Junior Sprints, Dirt Pro Trucks, Sport Compact, DIRTcar 4 Cylinders, Figure 8 - FWD Stock, Figure 8 - RWD-Stock, Figure 8 - RWD-Open | Results | | Jackson Gray (Winged A-Class) | 2nd | - | - | 1st |
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| 6/17/2023 | Warren County Speedway - Indianola, IA 2023 WC Race #6 Factory Stocks, Hobby Stocks, Stock Cars, Winged A-Class, Street Stocks, Hornets, Dirt Pro Trucks, Sport Compact | Results | | Jackson Gray (Winged A-Class) | 1st | - | - | 1st |
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| 6/24/2023 | Brooklyn Raceway - Brooklyn, IA Hobby Stocks, Stock Cars, Winged A-Class, Junior Sprints, Dirt Pro Trucks, Sport Compact, DIRTcar 4 Cylinders, Figure 8 - FWD Stock, Figure 8 - RWD-Stock, Figure 8 - RWD-Open | Results | | Jackson Gray (Winged A-Class) | 1st | - | - | 1st |
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| 7/3/2023 | Brooklyn Raceway - Brooklyn, IA Hobby Stocks, Stock Cars, Winged A-Class, Junior Sprints, Dirt Pro Trucks, Sport Compact, DIRTcar 4 Cylinders, Figure 8 - FWD Stock, Figure 8 - RWD-Stock, Figure 8 - RWD-Open | Results | | Jackson Gray (Winged A-Class) | 1st | - | - | 12th (DNF) |
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| 7/8/2023 | Warren County Speedway - Indianola, IA 2023 WC Race #8 Factory Stocks, Hobby Stocks, Stock Cars, Winged A-Class, Street Stocks, Hornets, Dirt Pro Trucks, Sport Compact | Results | | Jackson Gray (Winged A-Class) | 4th | - | - | 3rd |
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| 7/14/2023 | English Creek Speedway - Knoxville, IA Winged /Non Winged Micros Winged Outlaw, Winged A-Class, Stock Non-Wing, 600cc Modifieds, HART Non-Wing Micros | Results | | Jackson Gray (Winged Outlaw) | 3rd | - | - | 7th | | Jackson Gray (HART Non-Wing Micros) | 4th | - | - | 10th |
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| 7/22/2023 | Brooklyn Raceway - Brooklyn, IA Hobby Stocks, Stock Cars, Winged A-Class, Junior Sprints, Dirt Pro Trucks, Sport Compact, DIRTcar 4 Cylinders, Figure 8 - FWD Stock, Figure 8 - RWD-Stock, Figure 8 - RWD-Open | Results | | Jackson Gray (Winged A-Class) | 2nd | - | - | 1st |
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| 7/26/2023 | Warren County Speedway - Indianola, IA 2023 WC Race #9 - County Fair Race Factory Stocks, Hobby Stocks, Stock Cars, Winged A-Class, Street Stocks, Hornets, Dirt Pro Trucks, Sport Compact | Results | | Jackson Gray (Winged A-Class) | 2nd | - | - | 4th |
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| 7/28/2023 | KAM Raceway - Hastings, NE Restricted 'A' Class: NOW600 Restricted Micros Winged A-Class: NOW600 A-Class Micros Stock Non-Wing: NOW600 Non-Wing Micros | Results | | Jackson Gray (Winged A-Class) | 5th | - | 6th | - |
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| 7/29/2023 | KAM Raceway - Hastings, NE Restricted 'A' Class: NOW600 Restricted Micros Winged A-Class: NOW600 A-Class Micros Stock Non-Wing: NOW600 Non-Wing Micros | Results | | Jackson Gray (Winged A-Class) | 8th | - | DNS | - | | Jackson Gray (Stock Non-Wing) | 3rd | - | - | 20th |
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| 8/4/2023 | Brooklyn Raceway - Brooklyn, IA Brooklyn Raceway Hobby Stocks, Stock Cars, Winged A-Class, Junior Sprints, Dirt Pro Trucks, Sport Compact, IMCA Sport Compact, DIRTcar 4 Cylinders, Figure 8 - FWD Stock, Figure 8 - RWD-Stock, Figure 8 - RWD-Open | Results | | Jackson Gray (Winged A-Class) | 1st | - | - | 5th |
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| 8/19/2023 | Sweet Springs Motorsports Complex - Sweet Springs, MO Weekly Racing Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Jackson Gray (Winged A-Class) | 6th | - | - | 15th (DNF) |
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| 8/26/2023 | Warren County Speedway - Indianola, IA 2023 WC Race #11 Factory Stocks, Hobby Stocks, Stock Cars, Winged A-Class, Street Stocks, Hornets, Dirt Pro Trucks, Sport Compact | Results | | Jackson Gray (Winged A-Class) | 3rd | - | - | 3rd |
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| 9/1/2023 | Sweet Springs Motorsports Complex - Sweet Springs, MO Restricted 'A' Class: NOW600 Restricted Micros Winged A-Class: NOW600 A-Class Micros Stock Non-Wing: NOW600 Non-Wing Micros Winged Outlaw, Non-Wing Outlaw, Junior Sprints | Results | | Jackson Gray (Non-Wing Outlaw) | 7th | - | - | DNS | | Jackson Gray (Winged A-Class) | 3rd | - | 1st | 19th (DNF) |
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| 9/2/2023 | Sweet Springs Motorsports Complex - Sweet Springs, MO Restricted 'A' Class: NOW600 Restricted Micros Winged A-Class: NOW600 A-Class Micros Stock Non-Wing: NOW600 Non-Wing Micros Winged Outlaw, Non-Wing Outlaw, Junior Sprints | Results | | Jackson Gray (Non-Wing Outlaw) | 10th | - | 7th | - | | Jackson Gray (Winged A-Class) | 6th | - | 5th | - |
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| 9/3/2023 | Brooklyn Raceway - Brooklyn, IA Hobby Stocks, Stock Cars, Winged A-Class, Junior Sprints, Dirt Pro Trucks, Sport Compact, IMCA Sport Compact, DIRTcar 4 Cylinders, Figure 8 - FWD Stock, Figure 8 - RWD-Stock, Figure 8 - RWD-Open | Results | | Jackson Gray (Winged A-Class) | 1st | - | - | 4th |
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| 9/6/2023 | Sweet Springs Motorsports Complex - Sweet Springs, MO KKM Challenge Race Practice Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, 600cc Modifieds | Results | | Jackson Gray (Non-Wing Outlaw) | - | - | - | - | | Jackson Gray (Winged A-Class) | - | - | - | - |
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| 9/7/2023 | Sweet Springs Motorsports Complex - Sweet Springs, MO KKM Challenge Race Non-Wing Outlaw: POWRi 600cc Outlaw Micro Sprints Winged Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Jackson Gray (Non-Wing Outlaw) | - | - | - | - | | Jackson Gray (Winged A-Class) | 5th | - | - | 20th |
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| 9/8/2023 | Sweet Springs Motorsports Complex - Sweet Springs, MO KKM Challenge Race Non-Wing Outlaw: POWRi 600cc Outlaw Micro Sprints Winged Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Jackson Gray (Winged A-Class) | 4th | - | - | 12th |
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| 9/9/2023 | Sweet Springs Motorsports Complex - Sweet Springs, MO KKM Challenge Race - POWRi Non-Wing $10,000.00 to WIN Non-Wing Outlaw: POWRi 600cc Outlaw Micro Sprints Winged Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Jackson Gray (Winged A-Class) | - | - | 3rd | 4th |
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| 9/15/2023 | Brooklyn Raceway - Brooklyn, IA Hobby Stocks, Stock Cars, Winged A-Class, Junior Sprints, Dirt Pro Trucks, Sport Compact, IMCA Sport Compact, DIRTcar 4 Cylinders, Figure 8 - FWD Stock, Figure 8 - RWD-Stock, Figure 8 - RWD-Open | Results | | Jackson Gray (Winged A-Class) | 2nd | - | - | 7th (DNF) |
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| 9/16/2023 | Brooklyn Raceway - Brooklyn, IA 9/16 Brooklyn Nationals 2023 Hobby Stocks, Stock Cars, Winged A-Class, Junior Sprints, Dirt Pro Trucks, Sport Compact, IMCA Sport Compact, DIRTcar 4 Cylinders, Figure 8 - FWD Stock, Figure 8 - RWD-Stock, Figure 8 - RWD-Open | Results | | Jackson Gray (Winged A-Class) | 3rd (DNF) | - | - | 2nd |
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| 9/29/2023 | Sweet Springs Motorsports Complex - Sweet Springs, MO Weekly Racing Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Jackson Gray (Winged A-Class) | 2nd | - | - | 19th |
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| 9/30/2023 | Sweet Springs Motorsports Complex - Sweet Springs, MO Weekly Racing Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Jackson Gray (Winged A-Class) | 4th | - | - | 10th |
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| 10/12/2023 | Sweet Springs Motorsports Complex - Sweet Springs, MO Show Me Showdown in Memory of Dean Hathman Winged Outlaw, Non-Wing Outlaw, Winged A-Class, Sportsman Micros | Results | | Jackson Gray (Winged Outlaw) | - | - | - | - | | Jackson Gray (Winged A-Class) | 6th | - | - | 9th |
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| 10/13/2023 | Sweet Springs Motorsports Complex - Sweet Springs, MO Show Me Showdown in Memory of Dean Hathman Winged Outlaw, Restricted 'A' Class, Stock Non-Wing, Junior Sprints | Results | | Jackson Gray (Winged Outlaw) | 5th | - | - | 9th | | Jackson Gray (Stock Non-Wing) | 3rd | - | - | 15th |
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| 10/14/2023 | Sweet Springs Motorsports Complex - Sweet Springs, MO Show Me Showdown in Memory of Dean Hathman Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Jackson Gray (Winged Outlaw) | - | - | - | 9th | | Jackson Gray (Winged A-Class) | - | - | 2nd | 13th | | Jackson Gray (Stock Non-Wing) | - | - | 2nd | 11th |
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| 12/26/2023 | Tulsa Expo Raceway - Tulsa, OK Shootout Parking / Check-In Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints | Results | | Jackson Gray (Winged Outlaw) | - | - | - | - | | Jackson Gray (Non-Wing Outlaw) | - | - | - | - | | Jackson Gray (Winged A-Class) | - | - | - | - | | Jackson Gray (Stock Non-Wing) | - | - | - | - |
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| 12/27/2023 | Tulsa Expo Raceway - Tulsa, OK Morning Practice Then Racing Winged Outlaw: Tulsa Shootout | Results | | Jackson Gray (Winged Outlaw) | 6th | - | - | - |
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| 12/28/2023 | Tulsa Expo Raceway - Tulsa, OK Racing - Day 2 Winged Outlaw: Tulsa Shootout Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Jackson Gray (Winged Outlaw) | - | - | - | - | | Jackson Gray (Non-Wing Outlaw) | 9th | - | - | - | | Jackson Gray (Winged A-Class) | 8th | - | - | - |
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| 12/29/2023 | Tulsa Expo Raceway - Tulsa, OK Racing - Day 3 Non-Wing Outlaw, Winged A-Class, Stock Non-Wing, Junior Sprints | Results | | Jackson Gray (Non-Wing Outlaw) | - | - | - | - | | Jackson Gray (Winged A-Class) | - | - | - | - | | Jackson Gray (Stock Non-Wing) | 10th (DNF) | - | - | - |
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| 12/30/2023 | Tulsa Expo Raceway - Tulsa, OK Racing - Day 4 Winged Outlaw: Tulsa Shootout Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints | Results | | Jackson Gray (Winged Outlaw) | - | - | - | - | | Jackson Gray (Non-Wing Outlaw) | - | - | - | - | | Jackson Gray (Winged A-Class) | - | - | - | - | | Jackson Gray (Stock Non-Wing) | - | - | - | - |
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