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| 5/21/2021 | Farmer City Raceway - Farmer City, IL Weekly Show + B-Mods DIRTcar UMP Modifieds, Street Stocks, Dirt Late Models, Pro Late Model, DIRTcar Pro Modifieds | Results | | Chris Osborne Jr (DIRTcar UMP Modifieds) | 8th | - | - | 17th (DNF) |
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| 6/16/2021 | Peoria Speedway - Peoria, IL DIRTCAR SUMMER NATIONALS DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals | Results | | Chris Osborne Jr (DIRTcar UMP Modifieds) | 7th | - | - | 20th |
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| 6/23/2021 | LaSalle Speedway - Lasalle, IL DIRTCAR SUMMER NATIONALS DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals | Results | | Chris Osborne Jr (DIRTcar UMP Modifieds) | 7th | - | - | 14th |
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| 7/30/2021 | Fairbury Speedway - Fairbury, IL PRAIRIE DIRT CLASSIC Dirt Super Late Models: World of Outlaws - Late Models DIRTcar UMP Modifieds: DIRTcar Modified Nationals | Results | | Chris Osborne Jr (DIRTcar UMP Modifieds) | 9th | - | - | - |
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| 7/31/2021 | Fairbury Speedway - Fairbury, IL PRAIRIE DIRT CLASSIC Dirt Super Late Models: World of Outlaws - Late Models DIRTcar UMP Modifieds: DIRTcar Modified Nationals DIRTcar Late Models | Results | | Chris Osborne Jr (DIRTcar UMP Modifieds) | 9th | - | 22nd | - |
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| 8/21/2021 | Fairbury Speedway - Fairbury, IL FALS Cup Weekly Racing Fair Night DIRTcar Late Models, DIRTcar UMP Modifieds, DIRTcar Sportsmans, B Modifieds, Street Stocks | Results | | Chris Osborne Jr (DIRTcar UMP Modifieds) | 7th | - | - | 16th (DNF) |
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