| | Heat | Dash | B Feature | A Feature |
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| 4/3/2021 | Highland Speedway - Highland, IL DIRTcar Late Models, DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds, Street Stocks | Results | | Bret Eilerman (DIRTcar UMP Modifieds) | 2nd | - | - | 4th |
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| 4/17/2021 | Highland Speedway - Highland, IL DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds, Street Stocks | Results | | Bret Eilerman (DIRTcar UMP Modifieds) | 3rd | - | - | 4th |
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| 5/1/2021 | Highland Speedway - Highland, IL DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds, Street Stocks | Results | | Bret Eilerman (DIRTcar UMP Modifieds) | 5th | - | - | 4th |
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| 5/8/2021 | Highland Speedway - Highland, IL Nicci Egbert/Chris Bargetzi Memorial Race DIRTcar Late Models, DIRTcar UMP Modifieds, B Modifieds, Street Stocks | Results | | Bret Eilerman (DIRTcar UMP Modifieds) | 4th | - | - | 4th |
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| 5/15/2021 | Highland Speedway - Highland, IL DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds, Street Stocks | Results | | Bret Eilerman (DIRTcar UMP Modifieds) | 5th | - | - | 2nd |
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| 5/22/2021 | Highland Speedway - Highland, IL DIRTcar Late Models, DIRTcar UMP Modifieds, B Modifieds, Street Stocks | Results | | Bret Eilerman (DIRTcar UMP Modifieds) | 4th | - | - | 3rd |
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| 6/19/2021 | Highland Speedway - Highland, IL Grapperhaus Night of Destruction DIRTcar Late Models, DIRTcar UMP Modifieds, B Modifieds, Street Stocks | Results | | Bret Eilerman (DIRTcar UMP Modifieds) | 5th | - | - | 4th |
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| 7/17/2021 | Highland Speedway - Highland, IL Donnewald Distributing Night DIRTcar Late Models, DIRTcar UMP Modifieds, B Modifieds, Street Stocks | Results | | Bret Eilerman (DIRTcar UMP Modifieds) | 4th | - | - | 9th |
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| 7/24/2021 | Highland Speedway - Highland, IL Spectator Race DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds, Street Stocks | Results | | Bret Eilerman (DIRTcar UMP Modifieds) | 3rd | - | - | 5th |
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| 7/28/2021 | Highland Speedway - Highland, IL Madison County Fair Race DIRTcar Late Models, DIRTcar UMP Modifieds, B Modifieds, Street Stocks | Results | | Bret Eilerman (DIRTcar UMP Modifieds) | 6th | - | - | 18th |
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| 8/7/2021 | Highland Speedway - Highland, IL Leaps of Love DIRTcar Late Models, DIRTcar UMP Modifieds, B Modifieds, Street Stocks, Pure Stock | Results | | Bret Eilerman (DIRTcar UMP Modifieds) | 4th | - | - | 15th |
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| 8/13/2021 | Highland Speedway - Highland, IL Summer Nationals DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals B Modifieds, Street Stocks | Results | | Bret Eilerman (DIRTcar UMP Modifieds) | 5th | - | - | 7th |
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| 9/11/2021 | Highland Speedway - Highland, IL Bi State Late Models DIRTcar Late Models, DIRTcar UMP Modifieds, B Modifieds, Street Stocks | Results | | Bret Eilerman (DIRTcar UMP Modifieds) | 1st | - | - | 2nd |
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| 9/18/2021 | Highland Speedway - Highland, IL Championship NIght DIRTcar UMP Modifieds, Winged Outlaw, B Modifieds, Street Stocks | Results | | Bret Eilerman (DIRTcar UMP Modifieds) | 4th | - | - | 7th |
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