| | Heat | Dash | B Feature | A Feature |
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| 5/10/2019 | Belle-Clair Speedway - Belleville, IL Midwest Season Opener Midgets: POWRi National Midgets with POWRi Winged Outlaw, B Modifieds | Results | | Cailin Hunt (Winged Outlaw) | 5th | - | 14th | - |
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| 6/7/2019 | Coles County Speedway - Mattoon, IL AMSA 2500 to win Outlaw Wing Night 1 Winged Outlaw: American Micro Sprint Association Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Cailin Hunt (Winged Outlaw) | 2nd | - | - | - |
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| 6/13/2019 | Brownstown Bullring - Brownstown, IL Illinois SPEED Week Midgets: POWRi National Midgets Winged Outlaw | Results | | Cailin Hunt (Winged Outlaw) | 7th | - | 11th | - |
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| 6/14/2019 | Jacksonville Speedway - Jacksonville, IL Illinois SPEED Week Midgets: POWRi National Midgets Winged Outlaw | Results | | Cailin Hunt (Winged Outlaw) | 6th | - | - | - |
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| 9/6/2019 | Jacksonville Speedway - Jacksonville, IL Herb Barlow Memorial 410 Sprints - Winged: MOWA-Midwest Open Wheel Association Midgets: POWRi National Midgets Winged Outlaw | Results | | Cailin Hunt (Winged Outlaw) | 6th | - | - | 17th |
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| 9/13/2019 | Belle-Clair Speedway - Belleville, IL Midgets: POWRi Winged Outlaw | Results | | Cailin Hunt (Winged Outlaw) | 3rd | - | - | 10th |
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| 9/14/2019 | Macon Speedway - Macon, IL Midgets: POWRi Winged Outlaw, Winged A-Class, B Modifieds, Street Stocks | Results | | Cailin Hunt (Winged Outlaw) | 2nd | - | - | 16th | | Cailin Hunt (Winged A-Class) | - | - | - | 16th |
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| 10/5/2019 | Jacksonville Speedway - Jacksonville, IL 410 Sprints - Winged: MOWA-Midwest Open Wheel Association Midgets: POWRi National Midgets with POWRi 305 Sprints - Winged, Winged Outlaw | Results | | Cailin Hunt (Winged Outlaw) | 7th | - | - | 18th |
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