| | Heat | Dash | B Feature | A Feature |
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| 2/26/2021 | Southern Illinois Center - Duquoin, IL Midwest Winter Nationals Non-Wing Outlaw | Results | | Jeremy Bailey (Non-Wing Outlaw) | - | - | - | - |
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| 2/26/2021 | Wayne County Speedway - Wayne City, IL DuQuoin Winter Nationals - Week 1 - Night 1 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Lightning Sprints | Results | | Jeremy Bailey (Non-Wing Outlaw) | 5th | - | 8th | - |
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| 2/27/2021 | Southern Illinois Center - Duquoin, IL Midwest Winter Nationals Non-Wing Outlaw | Results | | Jeremy Bailey (Non-Wing Outlaw) | - | - | - | - |
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| 2/27/2021 | Wayne County Speedway - Wayne City, IL DuQuoin Winter Nationals - Week 1 - Night 2 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Lightning Sprints | Results | | Jeremy Bailey (Non-Wing Outlaw) | 5th | - | 8th | - |
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| 3/13/2021 | Wayne County Speedway - Wayne City, IL DuQuoin Winter Nationals - Week 3 - Night 2 Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Jeremy Bailey (Winged Outlaw) | 3rd | - | - | 11th |
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| 5/1/2021 | Southern Illinois Raceway - Marion, IL Points Begin Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Junior Sprints, Dwarf, 600cc Modifieds, Sportsman Micros | Results | | Jeremy Bailey (Winged Outlaw) | 4th | - | - | 8th |
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| 7/3/2021 | Wayne County Speedway - Wayne City, IL Season Opener Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, 600cc Modifieds | Results | | Jeremy Bailey (Winged Outlaw) | 2nd | - | - | 16th |
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