| | Heat | Dash | B Feature | A Feature |
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| 5/18/2019 | I-30 Speedway - Little Rock, AR Restricted 'A' Class: NOW600 Restricted Micros Winged A-Class: NOW600 A-Class Micros Stock Non-Wing: NOW600 Non-Wing Micros Winged Outlaw | Rain Out |
| 5/24/2019 | Sweet Springs Motorsports Complex - Sweet Springs, MO 1st Annual Show Me Nationals Midgets: POWRi National Midgets with POWRi West Midgets Winged Outlaw, Restricted 'A' Class | Rain Out |
| 5/25/2019 | Sweet Springs Motorsports Complex - Sweet Springs, MO 1st Annual Show Me Nationals Midgets: POWRi National Midgets with POWRi West Midgets Winged Outlaw, Restricted 'A' Class | Rain Out |
| 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 | | John Simpson II (Stock Non-Wing) | 9th | - | - | 21st |
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| 6/12/2019 | Caney Valley Speedway - Caney, KS Sooner 600 Week - Night 1 Restricted 'A' Class: NOW600 Restricted Micros Winged A-Class: NOW600 A-Class Micros Stock Non-Wing: NOW600 Non-Wing Micros Factory Stocks, Stock Cars, USRA B-Mods | Results | | John Simpson II (Stock Non-Wing) | - | - | - | - |
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| 6/21/2019 | Southern Illinois Raceway - Marion, IL Highbanks Hustle Winged A-Class | Results | | John Simpson II (Winged A-Class) | - | - | - | - |
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| 6/22/2019 | Southern Illinois Raceway - Marion, IL Highbanks Hustle Winged A-Class | Results | | John Simpson II (Winged A-Class) | - | - | - | - |
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| 7/4/2019 | Sweet Springs Motorsports Complex - Sweet Springs, MO John Hinck Championship Winged Outlaw | Rain Out |
| 7/5/2019 | Sweet Springs Motorsports Complex - Sweet Springs, MO John Hinck Championship Winged Outlaw | Results | | John Simpson II (Winged Outlaw) | - | - | - | - |
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| 7/6/2019 | Sweet Springs Motorsports Complex - Sweet Springs, MO John Hinck Championship Winged Outlaw | Results | | John Simpson II (Winged Outlaw) | - | - | - | - |
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| 7/10/2019 | Mitchell County Fairgrounds Raceway - Beloit, KS Midgets: USAC National Midgets Stock Non-Wing | Results | | John Simpson II (Stock Non-Wing) | - | - | - | - |
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| 7/12/2019 | Sweet Springs Motorsports Complex - Sweet Springs, MO Points Race for ALL Classes Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | John Simpson II (Stock Non-Wing) | 7th | - | - | 18th (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 | | John Simpson II (Winged Outlaw) | - | - | - | - |
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| 7/13/2019 | Valley Speedway - Grain Valley, MO Thunder in the Valley National midgets by Rod End Supply Midgets: POWRi National Midgets with POWRi West Midgets Winged Outlaw | Results | | John Simpson II (Winged Outlaw) | - | - | - | - |
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| 7/26/2019 | Southern Illinois Raceway - Marion, IL Terry Sprague Memorial Stock Non-Wing | Results | | John Simpson II (Stock Non-Wing) | - | - | - | - |
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| 7/27/2019 | Southern Illinois Raceway - Marion, IL Terry Sprague Memorial Stock Non-Wing | Results | | John Simpson II (Stock Non-Wing) | - | - | - | - |
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| 10/11/2019 | Belle-Clair Speedway - Belleville, IL Meents Memorial Midgets: POWRi National Midgets Winged Outlaw, B Modifieds | Postponed |
| 10/12/2019 | Southern Illinois Raceway - Marion, IL Southern Illinois Shootout Midgets: POWRi National Midgets Winged Outlaw | Results | | John Simpson II (Winged Outlaw) | - | - | - | - |
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| 11/2/2019 | Arkoma Speedway - Arkoma, OK Restricted 'A' Class: NOW600 Restricted Micros Winged A-Class: NOW600 A-Class Micros Stock Non-Wing: NOW600 Non-Wing Micros Sportsman Sprints, Sprint Cars, Junior Sprints | Results | | John Simpson II (Stock Non-Wing) | - | - | - | - |
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| 11/3/2019 | Arkoma Speedway - Arkoma, OK Restricted 'A' Class: NOW600 Restricted Micros Winged A-Class: NOW600 A-Class Micros Stock Non-Wing: NOW600 Non-Wing Micros Sportsman Sprints, Sprint Cars, Junior Sprints, Adult Medium, Adult Class, Enduro | Results | | John Simpson II (Stock Non-Wing) | - | - | - | - |
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