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| 5/8/2021 | Dells Raceway Park - Wisconsin Dells, WI Midwest Lifestyles Construction 59th Season Opener 6pm Asphalt Late Models, Midwest Modifieds, Bandits, Asphalt Sportsman Late Models | Results | | Ronnie Osborne (Bandits) | - | 2nd | - | 4th |
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| 5/15/2021 | Dells Raceway Park - Wisconsin Dells, WI Full Program-Weekly Racing Divisions 6pm Asphalt Late Models, Bandits, Pro Legends, Asphalt Sportsman Late Models | Results | | Ronnie Osborne (Bandits) | - | 1st | - | 3rd |
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| 5/29/2021 | Dells Raceway Park - Wisconsin Dells, WI Lyle Nabbefeldt 55 Tribute Night-CWRA Super Late Models 6pm Stock Cars, Bandits, Young Guns, Pro Legends, Asphalt Sportsman Late Models, Generic 1 | Results | | Ronnie Osborne (Bandits) | - | 2nd | - | 4th |
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| 6/12/2021 | Dells Raceway Park - Wisconsin Dells, WI Gandrud Chevrolet 50-Weekly Racing Divisions 6pm Asphalt Late Models, Bandits, Pro Legends, Asphalt Sportsman Late Models | Results | | Ronnie Osborne (Bandits) | - | 1st | - | 3rd |
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| 6/19/2021 | Dells Raceway Park - Wisconsin Dells, WI Apollo Tool Night-CWRA Super Late Models 6pm Asphalt Late Models, Stock Cars, Midwest Modifieds, Bandits, Asphalt Mini Trucks | Results | | Ronnie Osborne (Bandits) | - | 1st | - | 4th |
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| 6/25/2021 | Golden Sands Speedway - Plover, WI Fireworks/DB Vault Finale Asphalt Super Late Models, Hobby Stocks, Asphalt 4-Cylinders, Asphalt 4 cyl Modifieds | Results | | Ronnie Osborne (Asphalt 4-Cylinders) | 1st | - | - | 6th | | Ronnie Osborne (Asphalt 4 cyl Modifieds) | 3rd | - | - | 5th |
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| 7/10/2021 | Dells Raceway Park - Wisconsin Dells, WI Blystone Towing & Recovery 50-Weekly Racing Division 6pm Presented by Assembly Products Asphalt Late Models, Midwest Modifieds, Bandits, Asphalt Sportsman Late Models, Generic 1 | Results | | Ronnie Osborne (Bandits) | - | 2nd | - | 1st |
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| 7/17/2021 | Dells Raceway Park - Wisconsin Dells, WI O'Reilly's Auto Parts 50-CWRA Super Late Models 6pm Stock Cars, Bandits, Young Guns, Pro Legends, Asphalt Sport Mods | Results | | Ronnie Osborne (Bandits) | - | 3rd | - | 3rd |
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| 7/24/2021 | Dells Raceway Park - Wisconsin Dells, WI Incredible Cars of Cross Plains 50-Weekly Racing Divisions 6PM Asphalt Late Models, Midwest Modifieds, Bandits, Generic 1, Junior 2 Animal Asphalt Karting | Results | | Ronnie Osborne (Bandits) | - | 6th | - | 2nd |
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| 8/7/2021 | Dells Raceway Park - Wisconsin Dells, WI Weaver Auto Value Late Model 50-Racing 6PM Asphalt Late Models, Midwest Modifieds, Bandits, Pro Legends, Generic 1 | Rain Out |
| 8/21/2021 | Dells Raceway Park - Wisconsin Dells, WI SIX08 Graphics Late Model 50-5 Divisions of Racing 6pm Asphalt Late Models, Midwest Modifieds, Bandits, Pro Legends, Junior 2 Animal Asphalt Karting | Results | | Ronnie Osborne (Bandits) | - | 4th | - | 5th |
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| 8/28/2021 | Dells Raceway Park - Wisconsin Dells, WI Weaver Auto Value Parts Walbeck Classic-CWRA Super Late Models Stock Cars, Bandits, Asphalt Sportsman Late Models, Asphalt Pure Stocks, Generic 1 | Results | | Ronnie Osborne (Bandits) | - | 1st | - | 1st |
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| 9/11/2021 | Dells Raceway Park - Wisconsin Dells, WI Kalahari Resorts 2021 Season Championship Night Asphalt Late Models, Midwest Modifieds, Bandits, Pro Legends, Asphalt Sportsman Late Models | Results | | Ronnie Osborne (Bandits) | - | 2nd | - | 8th |
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| 9/25/2021 | Dells Raceway Park - Wisconsin Dells, WI Midwest Championship Weekend Saturday Presented by DRM Companies Asphalt Late Models, Stock Cars, Midwest Modifieds, Bandits, Pro Legends, Asphalt Pure Stocks | Results | | Ronnie Osborne (Bandits) | - | - | - | 4th |
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| 12/11/2021 | Dells Raceway Park - Wisconsin Dells, WI DRP Season Championship Banquet Chula Vista Resort 5pm Asphalt Late Models, Midwest Modifieds, Bandits, Pro Legends, Asphalt Sportsman Late Models, Asphalt Pure Stocks, Train Racing, Generic 1 | Results | | Ronnie Osborne (Bandits) | - | - | - | - |
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