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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 | | Jessee Holt (Winged Outlaw) | - | - | - | - | | Jessee Holt (Non-Wing Outlaw) | 1st | - | - | - |
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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 | | Jessee Holt (Winged Outlaw) | 3rd | - | - | - | | Jessee Holt (Non-Wing Outlaw) | - | - | - | - |
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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 | | Jessee Holt (Winged Outlaw) | - | 3rd | - | - | | Jessee Holt (Non-Wing Outlaw) | - | 10th | - | - |
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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 | | Jessee Holt (Winged Outlaw) | - | - | 4th | - | | Jessee Holt (Non-Wing Outlaw) | - | - | 3rd | - |
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| 5/4/2019 | Miami County Raceway - Peru, IN Points Race #1. $1000 to Win NW Outlaw! Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Jessee Holt (Winged Outlaw) | 1st | - | - | 2nd | | Jessee Holt (Non-Wing Outlaw) | 6th | - | 7th | - |
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| 5/18/2019 | Miami County Raceway - Peru, IN World Championship Final Tune-Up! Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Sportsman Micros | Results | | Jessee Holt (Non-Wing Outlaw) | 2nd | - | - | 5th |
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| 5/22/2019 | Miami County Raceway - Peru, IN Wednesday Night War presented by Engler Machine & Tool and Performance Electronics - Practice Night 305 Sprints - Winged, Midgets | Results | | Jessee Holt (305 Sprints - Winged) | - | - | - | - |
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| 5/23/2019 | Miami County Raceway - Peru, IN Performance Electronics Non-Wing World Championship Prelim Night #1 Non-Wing Outlaw | Results | | Jessee Holt (Non-Wing Outlaw) | 4th | - | 4th | - |
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| 5/24/2019 | Miami County Raceway - Peru, IN Performance Electronics Non-Wing World Championship Prelim Night #2 Non-Wing Outlaw | Results | | Jessee Holt (Non-Wing Outlaw) | 1st | - | 2nd | 10th |
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| 5/25/2019 | Miami County Raceway - Peru, IN Performance Electronics Non-Wing World Championship Non-Wing Outlaw | Results | | Jessee Holt (Non-Wing Outlaw) | 1st | - | 1st | 13th |
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| 6/1/2019 | Miami County Raceway - Peru, IN Points Race #3 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Jessee Holt (Winged Outlaw) | 4th | - | - | 1st | | Jessee Holt (Non-Wing Outlaw) | 1st | - | - | 2nd |
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| 6/8/2019 | Miami County Raceway - Peru, IN Points Race #4 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Jessee Holt (Winged Outlaw) | 3rd | - | - | 1st | | Jessee Holt (Non-Wing Outlaw) | 1st | - | - | 6th |
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| 6/22/2019 | Plymouth Speedway - Plymouth, IN Saturday Night Event Featuring Outlaw Super Street Challenge DIRTcar UMP Modifieds, Super Sports, Stock Non-Wing, Winged Crate Sprints | Results | | Jessee Holt (Stock Non-Wing) | 2nd | - | - | 2nd |
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| 7/3/2019 | Miami County Raceway - Peru, IN Firecracker 40's. $1000 to Win Non-Wing Outlaw and Outlaw Wing Plus Huge Fireworks Show! Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Jessee Holt (Winged Outlaw) | 2nd | - | - | 6th | | Jessee Holt (Non-Wing Outlaw) | 6th | - | DNS | - |
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| 7/13/2019 | Miami County Raceway - Peru, IN Points Race #5 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Jessee Holt (Winged Outlaw) | 3rd | - | - | 3rd | | Jessee Holt (Non-Wing Outlaw) | 1st | - | - | 5th |
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| 7/20/2019 | Miami County Raceway - Peru, IN Points Race #6 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Jessee Holt (Winged Outlaw) | 3rd | - | - | 2nd (DNF) | | Jessee Holt (Non-Wing Outlaw) | 2nd | - | - | 7th |
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| 8/24/2019 | Miami County Raceway - Peru, IN Points Race #8 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Jessee Holt (Winged Outlaw) | 3rd | - | - | 2nd | | Jessee Holt (Non-Wing Outlaw) | 1st | - | - | 2nd |
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| 8/31/2019 | Miami County Raceway - Peru, IN Points Race #9 - "Honoring Our Military" Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Jessee Holt (Winged Outlaw) | 3rd | - | - | 2nd | | Jessee Holt (Non-Wing Outlaw) | 4th | - | 1st | 9th |
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| 9/7/2019 | Miami County Raceway - Peru, IN The MAC / Points Race #10. $1000 to Win Outlaw NW! Double Points. Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Jessee Holt (Winged Outlaw) | 2nd | - | - | 2nd | | Jessee Holt (Non-Wing Outlaw) | 4th | - | 2nd | 13th |
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| 9/14/2019 | Miami County Raceway - Peru, IN Points Race #11 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Jessee Holt (Winged Outlaw) | 2nd | - | - | 7th (DNF) | | Jessee Holt (Non-Wing Outlaw) | 4th | - | - | DNS |
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| 9/28/2019 | Miami County Raceway - Peru, IN Points Race #12 - Season Championship! Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Sportsman Micros, Senior Micros | Results | | Jessee Holt (Winged Outlaw) | 1st | - | - | 3rd |
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