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| 1/23/2019 | East Bay Raceway Park - Tampa, FL 43rd Annual Winternationals DIRTcar UMP Modifieds, Street Stocks | Results | | Gary Bentley (DIRTcar UMP Modifieds) | 10th | - | 8th | - |
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| 1/24/2019 | East Bay Raceway Park - Tampa, FL 43rd Annual Winternationals DIRTcar UMP Modifieds, Street Stocks | Results | | Gary Bentley (DIRTcar UMP Modifieds) | 5th | - | 12th | - |
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| 1/25/2019 | East Bay Raceway Park - Tampa, FL 43rd Annual Winternationals DIRTcar UMP Modifieds, Street Stocks | Results | | Gary Bentley (DIRTcar UMP Modifieds) | DNS | - | DNS | - |
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| 1/26/2019 | East Bay Raceway Park - Tampa, FL 43rd Annual Winternationals DIRTcar UMP Modifieds, Street Stocks | Results | | Gary Bentley (DIRTcar UMP Modifieds) | 10th | - | DNS | - |
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| 2/5/2019 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals DIRTcar UMP Modifieds | Results | | Gary Bentley (DIRTcar UMP Modifieds) | 10th | - | 8th | - |
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| 2/6/2019 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals 410 Sprints - Winged: All Star Circuit of Champions DIRTcar UMP Modifieds | Results | | Gary Bentley (DIRTcar UMP Modifieds) | 4th | - | 11th | - |
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| 2/7/2019 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals 410 Sprints - Winged: All Star Circuit of Champions DIRTcar UMP Modifieds | Results | | Gary Bentley (DIRTcar UMP Modifieds) | 8th | - | 9th | - |
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| 2/8/2019 | Volusia Speedway Park - De Leon Springs, FL DirtCar Nationals 410 Sprints - Winged: World of Outlaws DIRTcar UMP Modifieds | Results | | Gary Bentley (DIRTcar UMP Modifieds) | - | - | - | - |
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| 2/9/2019 | Volusia Speedway Park - De Leon Springs, FL DirtCar Nationals 410 Sprints - Winged: World of Outlaws DIRTcar UMP Modifieds | Results | | Gary Bentley (DIRTcar UMP Modifieds) | 11th | - | 13th | - |
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| 2/11/2019 | Volusia Speedway Park - De Leon Springs, FL DIRTcar Nationals DIRTcar Late Models, DIRTcar UMP Modifieds | Results | | Gary Bentley (DIRTcar UMP Modifieds) | - | - | DNS | - |
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| 2/23/2019 | Tri City Speedway - Granite City, IL Tri City Awards Banquet DIRTcar Late Models, DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds, Street Stocks, Pro Late Model | Results | | Gary Bentley (DIRTcar UMP Modifieds) | - | - | - | - |
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| 3/23/2019 | Highland Speedway - Highland, IL Lucky 40 DIRTcar Late Models, DIRTcar UMP Modifieds, B Modifieds, Street Stocks | Results | | Gary Bentley (DIRTcar UMP Modifieds) | - | - | - | - |
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| 4/5/2019 | Farmer City Raceway - Farmer City, IL Dirt Super Late Models: World of Outlaws - Late Models A Modifieds, Street Stocks, Dirt Late Models, Pro Late Model | Results | | Gary Bentley (A Modifieds) | 11th | - | - | - |
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| 4/6/2019 | Farmer City Raceway - Farmer City, IL Dirt Super Late Models: World of Outlaws - Late Models A Modifieds, Street Stocks, Dirt Late Models, Pro Late Model | Results | | Gary Bentley (A Modifieds) | 11th | - | 6th | - |
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| 4/12/2019 | Tri City Speedway - Granite City, IL 410 Sprints - Winged: MOWA-Midwest Open Wheel Association DIRTcar Late Models, DIRTcar UMP Modifieds | Results | | Gary Bentley (DIRTcar UMP Modifieds) | 6th | - | 4th | - |
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| 4/20/2019 | Highland Speedway - Highland, IL Race night DIRTcar Late Models, DIRTcar UMP Modifieds, B Modifieds, Street Stocks | Results | | Gary Bentley (DIRTcar UMP Modifieds) | 3rd | - | - | 17th |
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| 4/21/2019 | Adams County Speedway (IL) - Quincy, IL Sunday Funday DIRTcar UMP Modifieds, Stock Cars, B Modifieds, Enduro, Sport Compact, Dirt Crate Late Models | Results | | Gary Bentley (DIRTcar UMP Modifieds) | 2nd | - | - | 7th |
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| 4/26/2019 | Farmer City Raceway - Farmer City, IL A Modifieds, B Modifieds, Street Stocks, Dirt Late Models, Pro Late Model | Results | | Gary Bentley (A Modifieds) | 4th | - | - | 12th |
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| 5/3/2019 | Lincoln Speedway - Lincoln, IL Ladies Night / $5.00 Ladies Admission in Grandstands Economy Midgets, DIRTcar UMP Modifieds, Street Stocks, Hornets, Pro Late Model | Results | | Gary Bentley (DIRTcar UMP Modifieds) | - | - | - | 18th |
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| 5/10/2019 | Farmer City Raceway - Farmer City, IL A Modifieds, Street Stocks, Dirt Late Models, Pro Late Model | Results | | Gary Bentley (A Modifieds) | 5th | - | - | 12th |
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| 5/17/2019 | Farmer City Raceway - Farmer City, IL A Modifieds, B Modifieds, Street Stocks, Dirt Late Models, Pro Late Model | Results | | Gary Bentley (A Modifieds) | 4th | - | - | 10th |
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| 5/18/2019 | Highland Speedway - Highland, IL Big 10 race DIRTcar Late Models, DIRTcar UMP Modifieds, B Modifieds, Street Stocks | Results | | Gary Bentley (DIRTcar UMP Modifieds) | 6th | - | DNS | - |
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