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| 1/2/2019 | Tulsa Expo Raceway - Tulsa, OK Practice/Heat Races Winged Outlaw: Tulsa Shootout Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Caleb Thompson (Non-Wing Outlaw) | 8th | - | - | - | | Caleb Thompson (Stock Non-Wing) | - | - | - | - |
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| 1/3/2019 | Tulsa Expo Raceway - Tulsa, OK Race Day Winged Outlaw: Tulsa Shootout Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Caleb Thompson (Non-Wing Outlaw) | - | - | - | - | | Caleb Thompson (Stock Non-Wing) | 3rd | - | - | - |
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| 1/4/2019 | Tulsa Expo Raceway - Tulsa, OK Race Day Winged Outlaw: Tulsa Shootout Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Caleb Thompson (Non-Wing Outlaw) | - | - | - | - | | Caleb Thompson (Stock Non-Wing) | - | - | - | - |
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| 1/5/2019 | Tulsa Expo Raceway - Tulsa, OK Shootout Finale - Golden Driller Day! Winged Outlaw: Tulsa Shootout Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Caleb Thompson (Non-Wing Outlaw) | - | - | - | - | | Caleb Thompson (Stock Non-Wing) | - | - | - | - |
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| 2/15/2019 | Hunt County Raceway - Greenville, TX Restricted 'A' Class: NOW600 Restricted Micros Winged A-Class: NOW600 A-Class Micros Stock Non-Wing: NOW600 Non-Wing Micros | Results | | Caleb Thompson (Stock Non-Wing) | 8th | - | 11th | - |
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| 2/16/2019 | Hunt County Raceway - Greenville, TX Restricted 'A' Class: NOW600 Restricted Micros Winged A-Class: NOW600 A-Class Micros Stock Non-Wing: NOW600 Non-Wing Micros | Results | | Caleb Thompson (Stock Non-Wing) | 7th | - | - | - |
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| 3/23/2019 | I-44 Riverside Speedway - Oklahoma City, OK POWRi Lucas Oil National & West Midget League, POWRi Outlaws & Non-Wing Midgets: POWRi National Midgets with POWRi West Midgets Winged Outlaw, Stock Non-Wing | Results | | Caleb Thompson (Stock Non-Wing) | 7th (DNF) | - | DNS | - |
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| 3/29/2019 | Port City Raceway - Tulsa, OK 8th Annual Donnie Ray Crawford Memorial Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Caleb Thompson (Stock Non-Wing) | 8th | - | 9th | - |
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| 3/30/2019 | Port City Raceway - Tulsa, OK 8th Annual Donnie Ray Crawford Memorial Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Caleb Thompson (Stock Non-Wing) | 8th | - | 5th | - |
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| 4/5/2019 | Red Dirt Raceway - Meeker, OK Non-Winged Sprints: United Sprint League Stock Non-Wing, B Modifieds, 360 Sprints - Non-Winged, Economy Sprints - Non Winged, Hornets, Champ 360 Sprints - Non Winged, Pure Stock | Results | | Caleb Thompson (Stock Non-Wing) | 7th | - | - | 11th |
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| 4/19/2019 | Red Dirt Raceway - Meeker, OK "Thunder Up" Night at the Track and FREE BIKE NIGHT - SUMMER SERIES Restricted 'A' Class, Stock Non-Wing, B Modifieds, Hornets, Pure Stock | Results | | Caleb Thompson (Stock Non-Wing) | 4th | - | - | 9th |
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| 4/20/2019 | I-44 Riverside Speedway - Oklahoma City, OK 6th Annual Blue Blast for Autism Awareness Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Caleb Thompson (Stock Non-Wing) | 7th (DNF) | - | 3rd | 13th |
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| 5/4/2019 | I-44 Riverside Speedway - Oklahoma City, OK Weekly Points Race Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Caleb Thompson (Non-Wing Outlaw) | 5th (DNF) | - | - | DNS |
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| 6/1/2019 | Red Dirt Raceway - Meeker, OK The Red Dirt Revival with the D.J. Bridwell Band and the Sprint Series of Oklahoma - SPECIAL EVENT 305 Sprints - Winged: SSO-Sprint Series of Oklahoma Restricted 'A' Class, Stock Non-Wing, Hornets, 600cc Modifieds | Results | | Caleb Thompson (Stock Non-Wing) | 5th (DNF) | - | - | DNS |
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| 6/7/2019 | I-44 Riverside Speedway - Oklahoma City, OK 20th Annual Micro Sprint Nationals Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Caleb Thompson (Non-Wing Outlaw) | 2nd | - | - | 9th |
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| 6/8/2019 | I-44 Riverside Speedway - Oklahoma City, OK 20th Annual Micro Sprint Nationals Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Caleb Thompson (Non-Wing Outlaw) | 5th | - | - | 11th |
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| 6/14/2019 | Red Dirt Raceway - Meeker, OK Sooner 600 Week - Night 3 Restricted 'A' Class: NOW600 Restricted Micros Winged A-Class: NOW600 A-Class Micros Stock Non-Wing: NOW600 Non-Wing Micros Non-Winged Sprints: United Sprint League B Modifieds, Hornets, Pure Stock | Results | | Caleb Thompson (Stock Non-Wing) | 6th | - | 17th | - |
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| 6/15/2019 | Port City Raceway - Tulsa, OK Sooner 600 Week - Night 4 Restricted 'A' Class: NOW600 Restricted Micros Winged A-Class: NOW600 A-Class Micros Stock Non-Wing: NOW600 Non-Wing Micros Winged Outlaw, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Caleb Thompson (Stock Non-Wing) | 7th | - | 8th | - |
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| 6/16/2019 | Arkoma Speedway - Arkoma, OK Sooner 600 Week - Finale Restricted 'A' Class: NOW600 Restricted Micros Winged A-Class: NOW600 A-Class Micros Stock Non-Wing: NOW600 Non-Wing Micros | Results | | Caleb Thompson (Stock Non-Wing) | 6th | - | 7th | - |
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| 6/21/2019 | Red Dirt Raceway - Meeker, OK Chandler Lions/Choctaw Yellowjackets FREE Night - SUMMER SERIES Winged Sprints, A Modifieds, Stock Non-Wing, B Modifieds, Hornets, 600cc Modifieds, Pure Stock | Results | | Caleb Thompson (Stock Non-Wing) | 2nd | - | - | 8th |
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| 6/22/2019 | I-44 Riverside Speedway - Oklahoma City, OK Weekly Points Race Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints | Results | | Caleb Thompson (Non-Wing Outlaw) | - | - | - | - | | Caleb Thompson (Winged A-Class) | 4th | - | - | 6th | | Caleb Thompson (Stock Non-Wing) | 2nd | - | - | 7th |
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| 6/29/2019 | I-44 Riverside Speedway - Oklahoma City, OK Weekly Points Race Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Caleb Thompson (Winged A-Class) | 3rd | - | - | 6th | | Caleb Thompson (Stock Non-Wing) | 2nd | - | - | 2nd |
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| 7/13/2019 | I-44 Riverside Speedway - Oklahoma City, OK 7th Annual Going Green for cancer Awareness Weekly Points Race Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints | Results | | Caleb Thompson (Winged A-Class) | 3rd | - | - | 13th (DNF) | | Caleb Thompson (Stock Non-Wing) | 6th (DNF) | - | - | 2nd |
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| 7/20/2019 | I-44 Riverside Speedway - Oklahoma City, OK Weekly Points Race Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Caleb Thompson (Stock Non-Wing) | 4th | - | - | 10th (DNF) |
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| 7/27/2019 | I-44 Riverside Speedway - Oklahoma City, OK POWRi West Midgets and Micros Weekly Points Race Midgets: POWRi West Midgets Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints | Results | | Caleb Thompson (Winged A-Class) | 7th (DNF) | - | - | DNS | | Caleb Thompson (Stock Non-Wing) | 4th | - | - | DNS |
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| 8/3/2019 | I-44 Riverside Speedway - Oklahoma City, OK Weekly Points Race Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Caleb Thompson (Non-Wing Outlaw) | 1st | - | - | 1st |
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| 8/10/2019 | I-44 Riverside Speedway - Oklahoma City, OK Weekly Points Race Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Caleb Thompson (Non-Wing Outlaw) | 5th | - | - | 3rd |
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| 8/17/2019 | I-44 Riverside Speedway - Oklahoma City, OK POWRi West Midgets & Micros for Grady Chandler Benefit & Auction Midgets: POWRi Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Caleb Thompson (Non-Wing Outlaw) | 4th | - | - | 13th (DNF) |
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| 8/24/2019 | I-44 Riverside Speedway - Oklahoma City, OK Weekly Points Race Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Caleb Thompson (Non-Wing Outlaw) | 2nd | - | - | 14th (DNF) |
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