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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 | | Garrett Duff (Winged Outlaw) | 12th | - | - | - | | Garrett Duff (Winged A-Class) | 4th | - | - | - |
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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 | | Garrett Duff (Winged Outlaw) | - | - | 13th | - | | Garrett Duff (Winged A-Class) | - | - | 3rd | - |
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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 | | Garrett Duff (Winged Outlaw) | 1st | - | - | 8th |
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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 | | Garrett Duff (Winged Outlaw) | 5th | - | 3rd | 8th |
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| 5/20/2016 | Brownstown Bullring - Brownstown, IL Midgets: POWRi National Midgets Stock Cars, Winged Outlaw | Results | | Garrett Duff (Midgets) | - | - | - | - | | Garrett Duff (Winged Outlaw) | 1st | - | - | 5th |
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| 5/21/2016 | Macon Speedway - Macon, IL Midgets: POWRi National Midgets Winged Outlaw, Street Stocks, Hornets, Pro Late Model | Results | | Garrett Duff (Winged Outlaw) | 1st | - | - | 4th |
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| 5/30/2016 | Macon Speedway - Macon, IL Night of NASCAR Stars Economy Midgets: POWRi Division II Midgets Midgets, DIRTcar UMP Modifieds, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Garrett Duff (Winged A-Class) | 2nd | - | - | 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 | | Garrett Duff (Winged Outlaw) | 4th | - | 2nd | 7th |
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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 | | Garrett Duff (Winged Outlaw) | 5th | - | - | 8th |
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| 6/17/2016 | Southern Illinois Raceway - Marion, IL High Banks Hustle IV - Night 1 Winged Outlaw | Results | | Garrett Duff (Winged Outlaw) | 10th (DNF) | - | - | - |
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| 6/18/2016 | Southern Illinois Raceway - Marion, IL High Banks Hustle IV - Finale Winged Outlaw | Results | | Garrett Duff (Winged Outlaw) | 8th (DNF) | - | - | - |
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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 | | Garrett Duff (Winged Outlaw) | 3rd | - | 1st | 17th |
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| 7/16/2016 | Southern Illinois Raceway - Marion, IL Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Dwarf, 600cc Modifieds | Results | | Garrett Duff (Winged Outlaw) | 3rd | - | - | 16th (DNF) |
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| 7/30/2016 | Macon Speedway - Macon, IL 410 Sprints - Winged: MOWA-Midwest Open Wheel Association Economy Midgets: POWRi Division II Midgets Winged A-Class, Hornets, Pro Late Model | Results | | Garrett Duff (Winged A-Class) | 2nd | - | - | 2nd |
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| 8/13/2016 | Macon Speedway - Macon, IL Eve of Destruction II FIREWORKS DIRTcar UMP Modifieds, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Garrett Duff (Winged A-Class) | 1st | - | - | 1st |
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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 | | Garrett Duff (Midgets) | - | - | - | - | | Garrett Duff (Winged Outlaw) | 2nd | - | - | 4th |
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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 | | Garrett Duff (Winged Outlaw) | 8th | - | 4th | 5th |
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| 9/10/2016 | Southern Illinois Raceway - Marion, IL Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints, Dwarf, 600cc Modifieds | Results | | Garrett Duff (Winged Outlaw) | 3rd | - | - | 7th |
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| 9/17/2016 | Macon Speedway - Macon, IL Skeff Distributing Pro Late Model Big Ten Championship DIRTcar UMP Modifieds, Winged A-Class, B Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Garrett Duff (Winged A-Class) | 2nd | - | - | 2nd |
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| 9/24/2016 | Macon Speedway - Macon, IL Season Championship Economy Midgets: POWRi Division II Midgets DIRTcar UMP Modifieds, DIRTcar Sportsmans, Winged A-Class, B Modifieds, Street Stocks, Hornets | Results | | Garrett Duff (Winged A-Class) | 2nd | - | - | 3rd |
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