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| 4/1/2016 | Belle-Clair Speedway - Belleville, IL Bob Johnston Classic DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Factory Stock, Stock Cars, Winged A-Class, B Modifieds | Results | | Carlee Gress (Winged A-Class) | 4th | - | - | 20th |
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| 4/15/2016 | Belle-Clair Speedway - Belleville, IL Non-Winged Sprints: POWRi WAR Sprints Stock Cars, Winged Outlaw, Stock Non-Wing, 410 Sprints - Non-Winged, Vintage Full Body Stock Cars, Dwarf | Results | | Carlee Gress (Winged Outlaw) | 1st | - | - | 9th |
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| 4/22/2016 | Jacksonville Speedway - Jacksonville, IL Economy Midgets: POWRi Division II Midgets 360 Sprints - Winged, Midgets, Winged Outlaw | Results | | Carlee Gress (Winged Outlaw) | 4th | - | - | 12th |
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| 4/29/2016 | Belle-Clair Speedway - Belleville, IL Midgets: POWRi National Midgets Stock Cars, Winged Outlaw, Dwarf | Results | | Carlee Gress (Winged Outlaw) | 6th | - | 8th | 10th |
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| 5/14/2016 | Southern Illinois Raceway - Marion, IL Non-Wing Outlaw: POWRi 600cc Outlaw Micro Sprints Winged Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, Dwarf, 600cc Modifieds | Results | | Carlee Gress (Winged Outlaw) | 4th | - | 1st | 14th |
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| 5/21/2016 | Southern Illinois Raceway - Marion, IL Weekly Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Dwarf, 600cc Modifieds | Results | | Carlee Gress (Winged Outlaw) | - | - | - | - |
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| 6/17/2016 | Southern Illinois Raceway - Marion, IL High Banks Hustle IV - Night 1 Winged Outlaw | Results | | Carlee Gress (Winged Outlaw) | 5th | - | - | - |
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| 6/18/2016 | Southern Illinois Raceway - Marion, IL High Banks Hustle IV - Finale Winged Outlaw | Results | | Carlee Gress (Winged Outlaw) | 6th | - | - | - |
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| 6/24/2016 | Belle-Clair Speedway - Belleville, IL Race around the Arch Midgets: POWRi National Midgets Stock Cars, Winged Outlaw, Dwarf | Results | | Carlee Gress (Winged Outlaw) | 3rd | - | - | 11th |
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| 7/9/2016 | Southern Illinois Raceway - Marion, IL Non-Wing Outlaw: POWRi 600cc Outlaw Micro Sprints Winged Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Dwarf, 600cc Modifieds | Results | | Carlee Gress (Winged Outlaw) | 4th | - | - | 7th |
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| 8/27/2016 | Southern Illinois Raceway - Marion, IL Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Dwarf, 600cc Modifieds | Results | | Carlee Gress (Non-Wing Outlaw) | 1st | - | - | 3rd |
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| 10/1/2016 | Belle-Clair Speedway - Belleville, IL Meents Memorial Midgets: POWRi National Midgets Winged Outlaw | Results | | Carlee Gress (Winged Outlaw) | 2nd | - | - | 8th |
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