| | Heat | Dash | B Feature | A Feature |
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| 5/30/2020 | Sweet Springs Motorsports Complex - Sweet Springs, MO Weekly Points Race Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Shain Kaiser (Winged Outlaw) | 5th | - | - | 8th |
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| 6/6/2020 | Sweet Springs Motorsports Complex - Sweet Springs, MO Gibson Memorial - Weekly Points Race Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Shain Kaiser (Winged Outlaw) | 7th | - | - | 14th |
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| 6/13/2020 | Sweet Springs Motorsports Complex - Sweet Springs, MO Weekly Points Race Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Shain Kaiser (Winged Outlaw) | 8th (DNF) | - | - | 11th (DNF) |
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| 6/20/2020 | Sweet Springs Motorsports Complex - Sweet Springs, MO Weekly Points Race Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Shain Kaiser (Winged Outlaw) | 1st | - | - | 5th |
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| 7/3/2020 | Sweet Springs Motorsports Complex - Sweet Springs, MO John Hinck Championship $20K to Win! Winged Outlaw Only Winged Outlaw | Results | | Shain Kaiser (Winged Outlaw) | 3rd | - | 17th | - |
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| 7/4/2020 | Sweet Springs Motorsports Complex - Sweet Springs, MO John Hinck Championship $20K to Win! Winged Outlaw Only Winged Outlaw | Results | | Shain Kaiser (Winged Outlaw) | DNS | - | - | - |
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| 7/11/2020 | Sweet Springs Motorsports Complex - Sweet Springs, MO Weekly Points Race Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Shain Kaiser (Winged Outlaw) | 3rd | - | - | 3rd |
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| 7/24/2020 | Southern Illinois Raceway - Marion, IL Engler Machine and Tool Highbanks Hustle Prelim Winged A-Class, Stock Non-Wing | Results | | Shain Kaiser (Winged A-Class) | 9th | - | 16th | - |
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| 7/25/2020 | Southern Illinois Raceway - Marion, IL Engler Machine and Tool Highbanks Hustle Final Winged A-Class, Stock Non-Wing | Results | | Shain Kaiser (Winged A-Class) | - | - | - | - |
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| 7/26/2020 | Southern Illinois Raceway - Marion, IL Highbanks Hustle Rain Delay Winged A-Class | Results | | Shain Kaiser (Winged A-Class) | 5th | - | - | - |
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| 8/22/2020 | Sweet Springs Motorsports Complex - Sweet Springs, MO Weekly Points Race Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Shain Kaiser (Winged Outlaw) | 8th (DNF) | - | - | - |
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| 10/9/2020 | Sweet Springs Motorsports Complex - Sweet Springs, MO ShowMe Showdown in Honor of Dean Hathman Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Shain Kaiser (Winged Outlaw) | 3rd | - | - | 24th (DNF) |
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| 10/10/2020 | Sweet Springs Motorsports Complex - Sweet Springs, MO ShowMe Showdown in Honor of Dean Hathman Championship Night Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Sportsman Micros | Results | | Shain Kaiser (Winged Outlaw) | - | - | 5th | 17th (DNF) |
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