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| 1/4/2020 | Tulsa Expo Raceway - Tulsa, OK #WintheDriller Winged Outlaw: Tulsa Shootout Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds |
| 1/17/2020 | Tulsa Expo Raceway - Tulsa, OK Vacuworx Global Qualifying Night Midgets: Chili Bowl Nationals | Results | | Chad Boespflug (Midgets) | 1st | 6th | 4th | 9th |
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| 1/18/2020 | Tulsa Expo Raceway - Tulsa, OK Lucas Oil Championship Night Midgets: Chili Bowl Nationals | Results | | Chad Boespflug (Midgets) | - | - | - | - |
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| 4/10/2020 | Lee County Speedway - Donnellson, IA 410 Sprints - Winged: IRA Interstate Racing Association | Canceled |
| 4/11/2020 | 34 Raceway - West Burlington, IA IRA & MOWA 410 Clash 410 Sprints - Winged: IRA Interstate Racing Association with MOWA-Midwest Open Wheel Association Limited Sport Mod, Sport Compact | Postponed |
| 4/25/2020 | Knoxville Raceway - Knoxville, IA Knoxville 410 Championship Points 410 Sprints - Winged | Results | | Chad Boespflug (410 Sprints - Winged) | - | - | - | - |
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| 4/25/2020 | Park Jefferson International Speedway - Jefferson, SD Open Wheel Nationals 410 Sprints - Winged, A Modifieds, IMCA Modified | Results | | Chad Boespflug (410 Sprints - Winged) | 3rd | - | - | 10th |
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| 5/8/2020 | Knoxville Raceway - Knoxville, IA 1st Race back ...no fans Invitational Only 48 Drivers 410 Sprints - Winged: World of Outlaws | Results | | Chad Boespflug (410 Sprints - Winged) | 9th | - | 15th | - |
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| 5/15/2020 | Jackson Motorplex - Jackson, MN Great Lakes Shootout presented by Harvey's Roofing & Tweeter Contracting - IRA Sprint Car Series 410 Sprints - Winged: IRA Interstate Racing Association 305 Sprints - Winged | Results | | Chad Boespflug (410 Sprints - Winged) | 4th | - | 7th | - |
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| 5/16/2020 | Jackson Motorplex - Jackson, MN Great Lakes Shootout presented by Tweeter Contracting and Harvey's Five Star Roofing 410 Sprints - Winged: IRA Interstate Racing Association | Rain Out |
| 5/22/2020 | Federated Auto Parts I-55 Raceway - Pevely, MO 410 Sprints - Winged: World of Outlaws | Results | | Chad Boespflug (410 Sprints - Winged) | - | - | - | - |
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| 5/23/2020 | Federated Auto Parts I-55 Raceway - Pevely, MO 410 Sprints - Winged: World of Outlaws with MOWA-Midwest Open Wheel Association DIRTcar UMP Modifieds, DIRTcar Sportsmans, DIRTcar Sport Compact, B Modifieds | Results | | Chad Boespflug (410 Sprints - Winged) | 10th | - | - | - |
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| 5/23/2020 | Knoxville Raceway - Knoxville, IA Midwest Power Series 360 Sprints 360 Sprints - Winged: Midwest Power Series 410 Sprints - Winged | Postponed |
| 5/29/2020 | Park Jefferson International Speedway - Jefferson, SD $6,600 to win 410 Sprints - Winged: IRA Interstate Racing Association with All Star Circuit of Champions B Modifieds | Results | | Chad Boespflug (410 Sprints - Winged) | 2nd | - | - | 23rd |
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| 5/30/2020 | Knoxville Raceway - Knoxville, IA 360 Sprints - Winged: Malvern Bank 360 Sprints with Nebraska 360 sprints 410 Sprints - Winged | Canceled |
| 5/30/2020 | Park Jefferson International Speedway - Jefferson, SD $6,600 to win 410 Sprints - Winged: IRA Interstate Racing Association with All Star Circuit of Champions Stock Cars | Results | | Chad Boespflug (410 Sprints - Winged) | 1st | 4th | - | 11th |
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| 6/3/2020 | I-80 Speedway - Greenwood, NE World of Outlaws NOS Energy Drink Sprint Cars 410 Sprints - Winged: World of Outlaws Dirt Late Models | Postponed |
| 6/6/2020 | Knoxville Raceway - Knoxville, IA 360 Sprints - Winged, 410 Sprints - Winged, Winged Crate Sprints | Results | | Chad Boespflug (410 Sprints - Winged) | 6th | - | 2nd | 20th |
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| 6/12/2020 | Knoxville Raceway - Knoxville, IA Brownells Big Guns Bash 410 Sprints - Winged: World of Outlaws 360 Sprints - Winged | Results | | Chad Boespflug (410 Sprints - Winged) | 11th | - | - | - |
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| 6/13/2020 | Knoxville Raceway - Knoxville, IA Brownells Big Guns Bash 410 Sprints - Winged: World of Outlaws 360 Sprints - Winged | Results | | Chad Boespflug (410 Sprints - Winged) | 11th | - | - | - |
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| 6/19/2020 | Dubuque Fairgrounds Speedway - Dubuque, IA World of Outlaws NOS Energy Drink Sprint Cars 410 Sprints - Winged | Canceled |
| 6/20/2020 | Knoxville Raceway - Knoxville, IA 360 Sprints - Winged, 410 Sprints - Winged, Winged Crate Sprints | Results | | Chad Boespflug (410 Sprints - Winged) | 5th | - | - | 17th |
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| 6/25/2020 | Jackson Motorplex - Jackson, MN AGCO Jackson Nationals featuring the World of Outlaws 410 Sprints - Winged: World of Outlaws 305 Sprints - Winged | Results | | Chad Boespflug (410 Sprints - Winged) | - | - | - | - |
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| 6/26/2020 | Jackson Motorplex - Jackson, MN AGCO Jackson Nationals featuring the World of Outlaws 410 Sprints - Winged: World of Outlaws Non Wing Crate Sprints: Wisconsin wingLESS Sprints | Results | | Chad Boespflug (410 Sprints - Winged) | - | - | - | - |
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| 6/27/2020 | Jackson Motorplex - Jackson, MN $30,000-to-win AGCO Jackson Nationals featuring the World of Outlaws 410 Sprints - Winged: World of Outlaws Non Wing Crate Sprints: Wisconsin wingLESS Sprints | Results | | Chad Boespflug (410 Sprints - Winged) | - | - | - | - |
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| 7/2/2020 | Cedar Lake Speedway - New Richmond, WI FVP Platinum Battery Showdown 410 Sprints - Winged: World of Outlaws 360 Sprints - Non-Winged: Traditional Sprint Car Series Dirt Super Late Models | Results | | Chad Boespflug (410 Sprints - Winged) | - | - | - | - |
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| 7/3/2020 | Cedar Lake Speedway - New Richmond, WI FVP Platinum Battery Showdown 410 Sprints - Winged: World of Outlaws Dirt Super Late Models | Results | | Chad Boespflug (410 Sprints - Winged) | - | - | - | - |
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| 7/10/2020 | 34 Raceway - West Burlington, IA World of Outlaws NOS Energy Drink Sprint Cars 410 Sprints - Winged: World of Outlaws 305 Sprints - Winged | Results | | Chad Boespflug (410 Sprints - Winged) | - | - | - | - |
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| 7/10/2020 | Knoxville Raceway - Knoxville, IA Corn Belt Nationals 410 Sprints - Non-Winged: USAC National Sprint Cars Non-Winged Sprints: POWRi WAR Sprints with Iowa Sprint Car League 360 Sprints - Winged, 410 Sprints - Winged | Results | | Chad Boespflug (410 Sprints - Winged) | - | - | - | - |
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| 7/11/2020 | Knoxville Raceway - Knoxville, IA Corn Belt Nationals 410 Sprints - Non-Winged: USAC National Sprint Cars Non-Winged Sprints: POWRi WAR Sprints with Iowa Sprint Car League 410 Sprints - Winged | Results | | Chad Boespflug (410 Sprints - Winged) | - | - | - | - |
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| 7/18/2020 | Knoxville Raceway - Knoxville, IA Midwest Power Series 360 Sprints 360 Sprints - Winged: Malvern Bank 360 Sprints with Nebraska 360 sprints, Midwest Power Series 410 Sprints - Winged | Results | | Chad Boespflug (410 Sprints - Winged) | - | - | - | - |
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| 7/31/2020 | Jackson Motorplex - Jackson, MN Richard White Memorial 410 Sprints - Winged, 305 Sprints - Winged | Postponed |
| 8/1/2020 | Knoxville Raceway - Knoxville, IA $5,000 to win 410 Sprints - Winged: All Star Circuit of Champions 360 Sprints - Winged | Results | | Chad Boespflug (410 Sprints - Winged) | - | - | - | - |
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| 8/9/2020 | Knoxville Raceway - Knoxville, IA Capitani Classic 410 Sprints - Winged | Results | | Chad Boespflug (410 Sprints - Winged) | - | - | - | - |
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| 8/13/2020 | Knoxville Raceway - Knoxville, IA NOS Energy Drink Knoxville Nationals Presented by Casey's General Stores 410 Sprints - Winged: World of Outlaws | Results | | Chad Boespflug (410 Sprints - Winged) | - | - | - | - |
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| 8/14/2020 | Knoxville Raceway - Knoxville, IA NOS Energy Drink Knoxville Nationals Presented by Casey's General Stores 410 Sprints - Winged: World of Outlaws | Results | | Chad Boespflug (410 Sprints - Winged) | - | - | - | - |
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| 8/15/2020 | Knoxville Raceway - Knoxville, IA NOS Energy Drink Knoxville Nationals Presented by Casey's General Stores 410 Sprints - Winged: World of Outlaws | Results | | Chad Boespflug (410 Sprints - Winged) | - | - | - | - |
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| 9/12/2020 | Cedar Lake Speedway - New Richmond, WI 20th Annual Jerry Richert Memorial 360 Sprints - Winged: Midwest Power Series 410 Sprints - Winged: IRA Interstate Racing Association Limited Sprints - Winged: Upper Midwest Sprint Car Series 360 Sprints - Non-Winged: Traditional Sprint Car Series Winged A-Class, 305 Sprints - Non-Winged | Results | | Chad Boespflug (410 Sprints - Winged) | - | - | - | - |
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| 9/17/2020 | Knoxville Raceway - Knoxville, IA 17th Annual Lucas Oil Late Model Nationals Dirt Super Late Models: Lucas Oil Late Model Dirt Series 410 Sprints - Winged | Canceled |
| 9/18/2020 | Knoxville Raceway - Knoxville, IA 17th Annual Lucas Oil Late Model Nationals Dirt Super Late Models: Lucas Oil Late Model Dirt Series 410 Sprints - Winged | Canceled |
| 9/19/2020 | Knoxville Raceway - Knoxville, IA 17th Annual Lucas Oil Late Model Nationals Dirt Super Late Models: SLMR Late Model Series with Lucas Oil Late Model Dirt Series 410 Sprints - Winged | Canceled |
| 9/25/2020 | Knoxville Raceway - Knoxville, IA | Results | | Chad Boespflug (410 Sprints - Winged) | - | - | - | - |
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| 10/16/2020 | Lakeside Speedway - Kansas City, KS FVP Platinum Battery Showdown 410 Sprints - Winged: World of Outlaws Mod Lites | Results | | Chad Boespflug (410 Sprints - Winged) | - | - | - | - |
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