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| 4/20/2019 | Cedar County Raceway - Tipton, IA IMCA Late Models: Deery Brothers Summer Series | Results | | Gary Webb (IMCA Late Models) | 9th | - | 8th | - |
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| 4/26/2019 | Davenport Speedway - Davenport, IA Koelher Electric Season Opener A Modifieds, B Modifieds, Street Stocks, Dirt Late Models, Sport Compact | Results | | Gary Webb (Dirt Late Models) | 4th | - | - | 8th |
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| 5/10/2019 | Davenport Speedway - Davenport, IA Davenport Speedway Weekly Racing A Modifieds, B Modifieds, Street Stocks, Dirt Late Models, Sport Compact | Results | | Gary Webb (Dirt Late Models) | 4th | - | - | 9th |
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| 5/16/2019 | Marshalltown Speedway - Marshalltown, IA Fast Shafts Dale DeFrance Memorial (Rescheduled Date) Hobby Stocks, A Modifieds, B Modifieds, Street Stocks, Dirt Late Models, Dwarf | Rain Out |
| 5/31/2019 | Davenport Speedway - Davenport, IA Quality Plus Auto Body Weekly Racing w/ Kenny Schrader A Modifieds, B Modifieds, Street Stocks, Dirt Late Models, Sport Compact | Results | | Gary Webb (Dirt Late Models) | 5th | - | - | 7th |
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| 6/7/2019 | Davenport Speedway - Davenport, IA Davenport Speedway Weekly Racing A Modifieds, B Modifieds, Street Stocks, Dirt Late Models, Sport Compact | Results | | Gary Webb (Dirt Late Models) | 2nd | - | - | 8th |
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| 6/14/2019 | Davenport Speedway - Davenport, IA Jumpin Joeys Night Weekly Racing A Modifieds, B Modifieds, Street Stocks, Dirt Late Models, Sport Compact | Results | | Gary Webb (Dirt Late Models) | 1st | - | - | 7th |
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| 6/18/2019 | Maquoketa Speedway - Maquoketa, IA IMCA Late Models: Deery Brothers Summer Series | Results | | Gary Webb (IMCA Late Models) | 7th | - | 5th | 23rd |
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| 6/27/2019 | Benton County Speedway - Vinton, IA IMCA Late Models: Deery Brothers Summer Series Hobby Stocks, Stock Cars, B Modifieds, 600cc Modifieds, Sport Compact | Results | | Gary Webb (IMCA Late Models) | 2nd | - | - | 17th |
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| 6/28/2019 | Davenport Speedway - Davenport, IA Jeff's Car Corner Night Weekly Racing A Modifieds, B Modifieds, Street Stocks, Dirt Late Models, Sport Compact | Results | | Gary Webb (Dirt Late Models) | 2nd | - | - | 5th |
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| 7/11/2019 | Marshalltown Speedway - Marshalltown, IA Haverhill Social Club Casey’s General Stores Night Fast Shafts Dale DeFrance / Bill Davis Memorial Hobby Stocks, A Modifieds, B Modifieds, Street Stocks, Dirt Late Models, Dwarf | Results | | Gary Webb (Dirt Late Models) | 6th | - | - | 12th |
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| 7/12/2019 | Davenport Speedway - Davenport, IA $1000 to win Late Models & Modifieds - Draw/Redraw all classes A Modifieds, B Modifieds, Street Stocks, Dirt Late Models, Sport Compact | Results | | Gary Webb (Dirt Late Models) | 4th | - | - | 10th |
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| 7/24/2019 | Fayette County Speedway - West Union, IA IMCA Late Models: Deery Brothers Summer Series Hobby Stocks, Stock Cars, USRA B-Mods, USRA Hobby Stocks, USRA Stock Cars | Results | | Gary Webb (IMCA Late Models) | 4th | - | - | 7th |
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| 7/26/2019 | Marshalltown Speedway - Marshalltown, IA Rumours Bar & Grill Salute to Marshalltown Police $1,000.00 to Win IMCA Modifieds Hobby Stocks, A Modifieds, B Modifieds, Street Stocks, Dirt Late Models, Dwarf | Results | | Gary Webb (Dirt Late Models) | 4th | - | - | 4th |
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| 8/2/2019 | Lee County Speedway - Donnellson, IA IMCA Late Models: Deery Brothers Summer Series Stock Cars, A Modifieds, B Modifieds, Sport Compact | Results | | Gary Webb (IMCA Late Models) | 5th | - | 10th | 16th |
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| 8/3/2019 | 34 Raceway - West Burlington, IA The New Mix 107.3 Night & High 5 for Kids Night - American Ordnance Employee Night 305 Sprints - Winged, A Modifieds, Dirt Late Models, Limited Sport Mod, Sport Compact | Results | | Gary Webb (Dirt Late Models) | 4th | - | - | 17th |
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| 8/16/2019 | Davenport Speedway - Davenport, IA Davenport Speedway Weekly Racing A Modifieds, B Modifieds, Street Stocks, Dirt Late Models, Sport Compact | Results | | Gary Webb (Dirt Late Models) | 3rd | - | - | 8th |
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| 8/18/2019 | Adams County Speedway (IL) - Quincy, IL IMCA Late Models: Deery Brothers Summer Series Stock Cars, Sport Compact | Results | | Gary Webb (IMCA Late Models) | 6th | - | - | 12th |
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| 8/23/2019 | Davenport Speedway - Davenport, IA Davenport Speedway Season Championship A Modifieds, B Modifieds, Street Stocks, Dirt Late Models, Sport Compact | Results | | Gary Webb (Dirt Late Models) | 4th | - | - | 6th |
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| 8/24/2019 | West Liberty Raceway - West Liberty, IA IMCA Late Models: Deery Brothers Summer Series | Results | | Gary Webb (IMCA Late Models) | 4th | - | - | 17th |
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| 9/2/2019 | Boone Speedway - Boone, IA IMCA Late Models: Deery Brothers Summer Series Hobby Stocks, B Modifieds | Results | | Gary Webb (IMCA Late Models) | 7th | - | 11th (DNF) | 18th |
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| 9/14/2019 | Peoria Speedway - Peoria, IL Fall Classic DIRTcar Late Models, DIRTcar UMP Modifieds, B Modifieds, Hornets | Results | | Gary Webb (DIRTcar Late Models) | 5th | - | - | 17th |
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| 10/12/2019 | I-80 Speedway - Greenwood, NE Speedway Motors Cornhusker Classic Dirt Super Late Models: SLMR Late Model Series Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Dirt Late Models, Sport Compact | Results | | Gary Webb (Dirt Super Late Models) | 4th | - | - | 23rd |
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