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| 1/1/2021 | Tulsa Expo Raceway - Tulsa, OK Racing Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints | Results | | Caden Englehart (Winged Outlaw) | - | 14th | - | - | | Caden Englehart (Winged A-Class) | - | 11th | - | - | | Caden Englehart (Stock Non-Wing) | - | 9th | 5th | - |
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| 1/2/2021 | Tulsa Expo Raceway - Tulsa, OK Driller Time! Winged Outlaw, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Stock Non-Wing, Junior Sprints, 600cc Modifieds | Results | | Caden Englehart (Winged Outlaw) | - | - | - | - | | Caden Englehart (Winged A-Class) | - | - | - | - |
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| 3/5/2021 | Wayne County Speedway - Wayne City, IL DuQuoin Winter Nationals - Week 2 - Night 1 Midgets, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Caden Englehart (Midgets) | - | - | - | - |
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| 3/6/2021 | Wayne County Speedway - Wayne City, IL DuQuoin Winter Nationals - Week 2 - Night 2 Midgets, Non-Wing Outlaw, Restricted 'A' Class, Winged A-Class, Junior Sprints | Results | | Caden Englehart (Midgets) | 5th | - | - | 9th |
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| 3/26/2021 | I-44 Riverside Speedway - Oklahoma City, OK Turnpike Challenge Midgets: POWRi National Midgets with POWRi West Midgets, POWRi Winged Outlaw, Stock Non-Wing | Results | | Caden Englehart (Midgets) | 4th | - | 5th | - |
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| 3/27/2021 | I-44 Riverside Speedway - Oklahoma City, OK Turnpike Challenge Midgets: POWRi National Midgets with POWRi West Midgets, POWRi Winged Outlaw, Winged A-Class | Results | | Caden Englehart (Midgets) | 2nd | - | - | 20th |
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| 3/28/2021 | Port City Raceway - Tulsa, OK Turnpike Challenge Midgets: POWRi National Midgets with POWRi West Midgets, POWRi Winged Outlaw | Results | | Caden Englehart (Midgets) | 5th | - | 8th | - |
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| 5/30/2021 | 141 Speedway - Maribel, WI Sunday Funday With the IRA Bumper to Bumper Sprint Cars 410 Sprints - Winged: IRA Interstate Racing Association Lightning Sprints: IRA Lightning Sprints Non Wing Crate Sprints: Wisconsin wingLESS Sprints | Results | | Caden Englehart (410 Sprints - Winged) | 8th | - | 6th | 17th |
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| 6/4/2021 | Lee County Speedway - Donnellson, IA 410 Sprints - Winged: MOWA-Midwest Open Wheel Association IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Sport Compact | Results | | Caden Englehart (410 Sprints - Winged) | 6th | - | - | 14th |
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| 6/6/2021 | Jacksonville Speedway - Jacksonville, IL 410 Sprints - Winged: MOWA-Midwest Open Wheel Association | Results | | Caden Englehart (410 Sprints - Winged) | 3rd | - | - | 19th |
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| 6/16/2021 | Charleston Speedway - Charleston, IL Illinois SPEED Week Midgets: POWRi National Midgets with POWRi Winged Outlaw | Results | | Caden Englehart (Midgets) | 5th | - | - | 18th |
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| 6/18/2021 | Jacksonville Speedway - Jacksonville, IL Illinois SPEED Week Midgets: POWRi National Midgets with POWRi Winged Outlaw | Results | | Caden Englehart (Midgets) | 7th | - | 13th | - |
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| 6/19/2021 | Macon Speedway - Macon, IL Illinois SPEED Week Midgets: POWRi National Midgets with POWRi Winged Outlaw, Winged A-Class, Street Stocks, Pro Late Model | Results | | Caden Englehart (Midgets) | 8th | - | 7th | - |
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| 6/20/2021 | Brownstown Bullring - Brownstown, IL Illinois SPEED Week Midgets: POWRi National Midgets with POWRi Winged Outlaw | Results | | Caden Englehart (Midgets) | DNS | - | - | 24th |
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| 6/26/2021 | Twin Cities Raceway Park - North Vernon, IN 410 Sprints - Winged: FASTonDIRT 305 Sprints - Winged | Results | | Caden Englehart (410 Sprints - Winged) | 5th | - | - | 14th |
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| 7/2/2021 | Attica Raceway Park - Attica, OH 410 Sprints - Winged, Dirt Late Models | Results | | Caden Englehart (410 Sprints - Winged) | 6th | - | - | 16th |
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| 7/3/2021 | Waynesfield Raceway Park - Waynesfield, OH 410 Sprints - Winged: FASTonDIRT 410 Sprints - Non-Winged: BOSS Buckeye Outlaw Sprint Series | Results | | Caden Englehart (410 Sprints - Winged) | 8th | - | 10th | - |
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| 7/22/2021 | Circle City Raceway - Indianapolis, IN Circle City Winged 410 Sprints, USAC Regional Midgets PLUS OUTLAW NON WINGED MICROS Midgets: USAC Indiana Midgets 410 Sprints - Winged, Non-Wing Outlaw | Results | | Caden Englehart (410 Sprints - Winged) | 5th | - | - | 11th |
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| 7/23/2021 | Jacksonville Speedway - Jacksonville, IL 410 Sprints - Winged, 305 Sprints - Winged | Results | | Caden Englehart (410 Sprints - Winged) | 2nd | - | - | 8th |
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| 7/30/2021 | Jacksonville Speedway - Jacksonville, IL 410 Sprints - Winged: MOWA-Midwest Open Wheel Association | Results | | Caden Englehart (410 Sprints - Winged) | 2nd | - | - | 13th |
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| 8/21/2021 | Atomic Speedway - Chillicothe, OH 410 Sprints - Winged: OVSCA-Ohio Valley Sprint Car Association | Results | | Caden Englehart (410 Sprints - Winged) | 8th | - | 7th | - |
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| 9/3/2021 | Jacksonville Speedway - Jacksonville, IL 410 Sprints - Winged, 305 Sprints - Winged | Results | | Caden Englehart (410 Sprints - Winged) | 4th (DNF) | - | - | 12th |
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| 9/4/2021 | Plymouth Dirt Track-Sheboygan Co Fair - Plymouth, WI Sheboygan County Fair 360 Sprints - Winged: MSA Sprint Car Association 410 Sprints - Winged: IRA Interstate Racing Association | Results | | Caden Englehart (410 Sprints - Winged) | 8th | - | 10th | - |
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| 9/5/2021 | 141 Speedway - Maribel, WI Sunday Funday - IRA Bumper to Bumper Sprint Cars with Grand Nationals, Street Stocks and Legends 410 Sprints - Winged: IRA Interstate Racing Association Stock Cars, Sportsmans | Results | | Caden Englehart (410 Sprints - Winged) | 7th | - | 6th | 21st |
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| 9/10/2021 | Jacksonville Speedway - Jacksonville, IL Herb Barlow Memorial 410 Sprints - Winged: MOWA-Midwest Open Wheel Association Midgets: POWRi National Midgets with POWRi Winged Outlaw | Results | | Caden Englehart (410 Sprints - Winged) | 4th | - | - | 13th |
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| 9/11/2021 | Spoon River Speedway - Canton, IL Tom Knowles Memorial 410 Sprints - Winged: MOWA-Midwest Open Wheel Association Midgets: POWRi National Midgets with POWRi | Results | | Caden Englehart (410 Sprints - Winged) | 4th | - | - | 19th |
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