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| 1/1/2016 | Tulsa Expo Raceway - Tulsa, OK Racing Midgets, Economy Midgets, Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, 410 Sprints - Non-Winged, Junior Sprints, 1200cc Outlaws Non-Winged Minis, 1200cc Outlaws Winged Minis | Results | | Nathan Benson (Winged Outlaw) | 10th | - | - | - | | Nathan Benson (Non-Wing Outlaw) | - | - | - | - | | Nathan Benson (Winged A-Class) | 1st | - | - | - | | Nathan Benson (Stock Non-Wing) | 7th | - | 1st | - |
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| 1/2/2016 | Tulsa Expo Raceway - Tulsa, OK Racing Midgets, Economy Midgets, Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, 410 Sprints - Non-Winged, Junior Sprints, 1200cc Outlaws Non-Winged Minis, 1200cc Outlaws Winged Minis | Results | | Nathan Benson (Winged Outlaw) | - | - | 7th | - | | Nathan Benson (Non-Wing Outlaw) | - | - | 14th (DNF) | - | | Nathan Benson (Winged A-Class) | - | - | - | 6th | | Nathan Benson (Stock Non-Wing) | 2nd | - | - | 20th (DNF) |
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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 | | Nathan Benson (Winged Outlaw) | 2nd | - | - | 1st |
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| 4/22/2016 | Jacksonville Speedway - Jacksonville, IL Economy Midgets: POWRi Division II Midgets 360 Sprints - Winged, Midgets, Winged Outlaw | Results | | Nathan Benson (Winged Outlaw) | 2nd | - | - | 2nd |
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| 4/23/2016 | Macon Speedway - Macon, IL Midgets: POWRi National Midgets Economy Midgets: POWRi Division II Midgets Winged Outlaw, Street Stocks | Results | | Nathan Benson (Winged Outlaw) | 4th | - | - | 4th |
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| 4/29/2016 | Belle-Clair Speedway - Belleville, IL Midgets: POWRi National Midgets Stock Cars, Winged Outlaw, Dwarf | Results | | Nathan Benson (Winged Outlaw) | 1st | - | - | 1st |
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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 | | Nathan Benson (Winged Outlaw) | 3rd | - | - | 2nd |
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| 5/20/2016 | Brownstown Bullring - Brownstown, IL Midgets: POWRi National Midgets Stock Cars, Winged Outlaw | Results | | Nathan Benson (Midgets) | - | - | - | - | | Nathan Benson (Winged Outlaw) | 1st | - | - | 2nd |
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| 5/21/2016 | Macon Speedway - Macon, IL Midgets: POWRi National Midgets Winged Outlaw, Street Stocks, Hornets, Pro Late Model | Results | | Nathan Benson (Winged Outlaw) | 2nd | - | - | 2nd |
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| 6/8/2016 | Belle-Clair Speedway - Belleville, IL Speed Week Midgets: POWRi National Midgets Economy Midgets: POWRi Division II Midgets Stock Cars, Winged Outlaw | Results | | Nathan Benson (Winged Outlaw) | 1st | - | - | 3rd |
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| 6/9/2016 | Adams County Speedway (IL) - Quincy, IL Midgets: POWRi National Midgets Economy Midgets: POWRi Division II Midgets Winged Outlaw | Results | | Nathan Benson (Winged Outlaw) | 1st | - | - | 9th |
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| 6/10/2016 | Jacksonville Speedway - Jacksonville, IL Speed Week Midgets: POWRi National Midgets Economy Midgets: POWRi Division II Midgets Winged Outlaw | Results | | Nathan Benson (Winged Outlaw) | 1st | - | - | 2nd |
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| 6/11/2016 | Macon Speedway - Macon, IL Speed Week Midgets: POWRi National Midgets Economy Midgets: POWRi Division II Midgets Stock Cars, Winged Outlaw, Pro Late Model | Results | | Nathan Benson (Winged Outlaw) | 1st | - | - | 4th |
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| 6/12/2016 | Lincoln Speedway - Lincoln, IL Illinois SPEED Week Midgets: POWRi National Midgets Economy Midgets: POWRi Division II Midgets DIRTcar UMP Modifieds, Winged Outlaw | Results | | Nathan Benson (Winged Outlaw) | 3rd | - | - | 3rd |
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| 6/17/2016 | Southern Illinois Raceway - Marion, IL High Banks Hustle IV - Night 1 Winged Outlaw | Results | | Nathan Benson (Winged Outlaw) | 1st | - | - | 7th |
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| 6/18/2016 | Southern Illinois Raceway - Marion, IL High Banks Hustle IV - Finale Winged Outlaw | Results | | Nathan Benson (Winged Outlaw) | 1st | - | - | 4th |
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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 | | Nathan Benson (Winged Outlaw) | 2nd | - | - | 22nd |
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| 6/25/2016 | Farmington Empire Speedway - Farmington, MO Race around the Arch Midgets: POWRi National Midgets 410 Sprints - Winged, Winged Outlaw | Results | | Nathan Benson (Winged Outlaw) | 1st | - | - | 2nd |
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| 7/22/2016 | Champaign County Speedway - Champaign, IL Economy Midgets: POWRi Division II Midgets Winged Outlaw | Results | | Nathan Benson (Winged Outlaw) | 3rd | - | - | 1st |
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| 7/29/2016 | Southern Illinois Raceway - Marion, IL Terry Sprague Memorial Stock Non-Wing | Results | | Nathan Benson (Stock Non-Wing) | 2nd | - | 1st | 7th |
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| 7/30/2016 | Southern Illinois Raceway - Marion, IL Terry Sprague Memorial Stock Non-Wing | Results | | Nathan Benson (Stock Non-Wing) | 5th | - | 5th | 24th (DNF) |
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| 8/5/2016 | Sweet Springs Motorsports Complex - Sweet Springs, MO Restricted 'A' Class: NOW600 National Micros with NOW600 Restricted Micros Winged A-Class: NOW600 A-Class Micros Stock Non-Wing: NOW600 Non-Wing Micros | Results | | Nathan Benson (Winged A-Class) | 2nd | - | - | 1st | | Nathan Benson (Stock Non-Wing) | - | - | - | - |
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| 8/6/2016 | Sweet Springs Motorsports Complex - Sweet Springs, MO Restricted 'A' Class: NOW600 National Micros with NOW600 Restricted Micros Winged A-Class: NOW600 A-Class Micros Stock Non-Wing: NOW600 Non-Wing Micros | Results | | Nathan Benson (Winged A-Class) | - | 1st | - | 22nd |
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| 8/19/2016 | Lincoln Speedway - Lincoln, IL Springfield Fair Midgets: POWRi National Midgets DIRTcar UMP Modifieds, Winged Outlaw, Pro Late Model | Results | | Nathan Benson (Midgets) | - | - | - | - | | Nathan Benson (Winged Outlaw) | 1st | - | - | 1st |
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| 8/20/2016 | Macon Speedway - Macon, IL Camfield Memorial Midgets: POWRi National Midgets Winged Outlaw, Street Stocks, Hornets, Pro Late Model | Results | | Nathan Benson (Winged Outlaw) | 1st | - | - | 1st |
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| 9/17/2016 | I-30 Speedway - Little Rock, AR 600 World Championship - Finale Midgets: POWRi West Midgets 360 Sprints - Winged, Winged Outlaw | Results | | Nathan Benson (Winged Outlaw) | 3rd | - | - | 3rd |
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| 12/26/2016 | Tulsa Expo Raceway - Tulsa, OK Early Parking Economy Midgets, Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 1200cc Outlaws Non-Winged Minis, 1200cc Outlaws Winged Minis | Results | | Nathan Benson (Winged Outlaw) | - | - | - | - | | Nathan Benson (Winged A-Class) | - | - | - | - |
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| 12/28/2016 | Tulsa Expo Raceway - Tulsa, OK Practice / Races Winged Outlaw: Tulsa Shootout Economy Midgets, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 1200cc Outlaws Non-Winged Minis, 1200cc Outlaws Winged Minis | Results | | Nathan Benson (Winged Outlaw) | - | - | - | - | | Nathan Benson (Winged A-Class) | - | - | - | - |
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| 12/29/2016 | Tulsa Expo Raceway - Tulsa, OK Races Winged Outlaw: Tulsa Shootout Economy Midgets, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 1200cc Outlaws Non-Winged Minis, 1200cc Outlaws Winged Minis | Results | | Nathan Benson (Winged Outlaw) | 1st | - | - | - | | Nathan Benson (Winged A-Class) | - | - | - | - |
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| 12/30/2016 | Tulsa Expo Raceway - Tulsa, OK Races Winged Outlaw: Tulsa Shootout Economy Midgets, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 1200cc Outlaws Non-Winged Minis, 1200cc Outlaws Winged Minis | Results | | Nathan Benson (Winged Outlaw) | - | - | - | - | | Nathan Benson (Winged A-Class) | 2nd | - | - | - |
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| 12/31/2016 | Tulsa Expo Raceway - Tulsa, OK Races Winged Outlaw: Tulsa Shootout Economy Midgets, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 1200cc Outlaws Non-Winged Minis, 1200cc Outlaws Winged Minis | Results | | Nathan Benson (Winged Outlaw) | - | - | - | - | | Nathan Benson (Winged A-Class) | - | - | - | - |
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