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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 | | Garet Williamson (Winged Outlaw) | - | - | - | - | | Garet Williamson (Non-Wing Outlaw) | 9th | - | - | - |
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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 | | Garet Williamson (Winged Outlaw) | 3rd | - | - | - | | Garet Williamson (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 | | Garet Williamson (Winged Outlaw) | - | 7th | - | - | | Garet Williamson (Non-Wing Outlaw) | - | - | - | - |
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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 | | Garet Williamson (Winged Outlaw) | - | - | 7th | - | | Garet Williamson (Non-Wing Outlaw) | - | - | - | - |
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| 1/16/2019 | Tulsa Expo Raceway - Tulsa, OK Racing Night 3 Midgets: Chili Bowl Nationals | Results | | Garet Williamson (Midgets) | 5th | - | - | - |
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| 1/19/2019 | Tulsa Expo Raceway - Tulsa, OK Racing Night 6 Midgets: Chili Bowl Nationals | Results | | Garet Williamson (Midgets) | - | - | - | - |
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| 3/9/2019 | Southern Illinois Center - Duquoin, IL Midgets: USAC National Midgets Winged Outlaw | Results | | Garet Williamson (Midgets) | 8th | - | - | - |
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| 4/27/2019 | Sweet Springs Motorsports Complex - Sweet Springs, MO Non-Points Race for all Classes Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Garet Williamson (Stock Non-Wing) | 3rd | - | - | 3rd |
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| 5/26/2019 | Lake Ozark Speedway - Eldon, MO 360 Sprints - Winged: ASCS National with ASCS Warrior Region Midgets: POWRi National Midgets with POWRi West Midgets | Results | | Garet Williamson (Midgets) | 6th | - | - | 16th |
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| 6/1/2019 | Sweet Springs Motorsports Complex - Sweet Springs, MO Jr. Sprints Night to Shine - Points Race for ALL Classes Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Garet Williamson (Stock Non-Wing) | 1st | - | - | 18th (DNF) |
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| 6/8/2019 | Sweet Springs Motorsports Complex - Sweet Springs, MO Chase and Rodney Gibson Memorial - Points race for ALL classes Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Garet Williamson (Winged Outlaw) | 10th | - | - | 25th (DNF) |
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| 6/21/2019 | Southern Illinois Raceway - Marion, IL Highbanks Hustle Winged A-Class | Results | | Garet Williamson (Winged A-Class) | - | - | - | - |
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| 7/5/2019 | Sweet Springs Motorsports Complex - Sweet Springs, MO John Hinck Championship Winged Outlaw | Results | | Garet Williamson (Winged Outlaw) | 5th | - | 6th | 15th |
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| 7/6/2019 | Sweet Springs Motorsports Complex - Sweet Springs, MO John Hinck Championship Winged Outlaw | Results | | Garet Williamson (Winged Outlaw) | 1st | - | 15th (DNF) | - |
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| 7/12/2019 | Valley Speedway - Grain Valley, MO Thunder In the Valley National Midgets by Rod End Supply Midgets: POWRi National Midgets with POWRi West Midgets Sprint Cars, Winged Outlaw | Results | | Garet Williamson (Midgets) | 7th | - | 18th | - |
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| 8/31/2019 | Lake Ozark Speedway - Eldon, MO 360 Sprints - Winged: ASCS National with ASCS Warrior Region Midgets: POWRi National Midgets with POWRi West Midgets | Results | | Garet Williamson (360 Sprints - Winged) | 1st | - | - | 17th (DNF) |
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| 9/1/2019 | Lake Ozark Speedway - Eldon, MO 360 Sprints - Winged: ASCS National with ASCS Warrior Region Midgets: POWRi National Midgets with POWRi West Midgets | Results | | Garet Williamson (360 Sprints - Winged) | 4th | - | 5th | - |
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| 9/14/2019 | Lake Ozark Speedway - Eldon, MO Weekly Show #19 End of Season Championship Dirt Late Models: United Late Model Association 360 Sprints - Winged, 305 Sprints - Winged, Street Stocks, Pure Stock, USRA B-Mods, USRA Modifieds | Results | | Garet Williamson (360 Sprints - Winged) | 5th | - | - | 8th |
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| 9/19/2019 | Lucas Oil Speedway - Wheatland, MO 360 Sprints - Winged: ASCS National with ASCS Warrior Region Non-Winged Sprints: POWRi WAR Sprints | Results | | Garet Williamson (360 Sprints - Winged) | 7th | - | 16th | - |
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| 9/20/2019 | Lucas Oil Speedway - Wheatland, MO 360 Sprints - Winged: ASCS National with ASCS Warrior Region Non-Winged Sprints: POWRi WAR Sprints | Results | | Garet Williamson (360 Sprints - Winged) | 8th | - | 10th | - |
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| 9/21/2019 | Lucas Oil Speedway - Wheatland, MO 360 Sprints - Winged: ASCS National with ASCS Warrior Region Non-Winged Sprints: POWRi WAR Sprints | Results | | Garet Williamson (360 Sprints - Winged) | 7th | - | 7th | - |
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| 10/5/2019 | Lake Ozark Speedway - Eldon, MO Midwest Lighting Sprint Nationals + ASCS 360 Warrior Sprints 360 Sprints - Winged: ASCS Warrior Region Lightning Sprints | Results | | Garet Williamson (360 Sprints - Winged) | 5th | - | - | 10th |
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| 10/12/2019 | Creek County Speedway - Sapulpa, OK Fall Fling 360 Sprints - Winged: ASCS National with ASCS Sooner Region Non-Winged Sprints: United Sprint League | Results | | Garet Williamson (360 Sprints - Winged) | 6th | - | 6th | 16th |
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| 10/19/2019 | Lake Ozark Speedway - Eldon, MO Jason Johnson Classic / World Of Outlaws ! Invades For 2nd Time In 2019! 410 Sprints - Winged: World of Outlaws 305 Sprints - Winged | Results | | Garet Williamson (305 Sprints - Winged) | 5th | - | - | 7th |
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