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| 5/15/2020 | Crawford County Speedway - Denison, IA Dirt Late Models: Tri-State Late Models Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Hornets, Sport Compact | Results | | Jason O'Brien (Dirt Late Models) | 5th | - | - | 8th |
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| 5/16/2020 | Park Jefferson International Speedway - Jefferson, SD $2000 to Win Tri State Late Models plus IMCA Weekly Racing Season Opener Dirt Late Models: Tri-State Late Models 305 Sprints - Winged, Dirt Super Late Models, Hobby Stocks, Stock Cars, B Modifieds, Hornets | Rain Out |
| 5/24/2020 | Stuart Speedway - Stuart, IA Stuart Speedway - WEST Dirt Super Late Models: SLMR Late Model Series Hobby Stocks, Stock Cars, B Modifieds, Dwarf, 600cc Modifieds | Rain Out |
| 5/30/2020 | Central Missouri Speedway - Warrensburg, MO Race #3 - SLMR Late Models! Dirt Super Late Models: SLMR Late Model Series A Modifieds, B Modifieds, Street Stocks, Mod Lites | Results | | Jason O'Brien (Dirt Super Late Models) | 1st | - | - | 19th |
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| 6/10/2020 | Stuart Speedway - Stuart, IA SLMR Late Models Dirt Super Late Models: SLMR Late Model Series Stock Cars, A Modifieds, B Modifieds, 600cc Modifieds, IMCA Modified | Results | | Jason O'Brien (Dirt Super Late Models) | 1st | - | - | 9th |
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| 6/12/2020 | I-80 Speedway - Greenwood, NE I-80 Dirt Classic Dirt Super Late Models: SLMR Late Model Series Stock Cars, A Modifieds, B Modifieds, Sport Compact | Results | | Jason O'Brien (Dirt Super Late Models) | 5th | - | - | 12th |
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| 7/18/2020 | Shelby County Speedway - Harlan, IA Shelby County Speedway - WEST Dirt Super Late Models: SLMR Late Model Series Stock Cars, B Modifieds, Sport Compact | Results | | Jason O'Brien (Dirt Super Late Models) | 3rd | - | - | 3rd |
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| 7/22/2020 | I-80 Speedway - Greenwood, NE Prelude to the Silver Dollar Nationals Dirt Super Late Models: SLMR Late Model Series A Modifieds, IMCA Modified | Results | | Jason O'Brien (Dirt Super Late Models) | 4th | - | - | 12th |
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| 8/1/2020 | Adams County Speedway - Corning, IA Ray Houck Memorial--Malvern Bank SLMR Late Models $3,000 to win, Presented by Dirt Track Bank Dirt Super Late Models: SLMR Late Model Series Hobby Stocks, Stock Cars, A Modifieds, B Modifieds, Sport Compact | Results | | Jason O'Brien (Dirt Super Late Models) | 4th | - | - | 22nd |
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| 8/28/2020 | I-80 Speedway - Greenwood, NE I-80 Speedway Dirt Super Late Models: SLMR Late Model Series Stock Cars, A Modifieds, Dirt Late Models, Sport Compact | Results | | Jason O'Brien (Dirt Super Late Models) | 2nd | - | - | 5th |
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| 8/29/2020 | Off Road Speedway - Norfolk, NE Bob Haase Memorial with Super Late Models Dirt Super Late Models: SLMR Late Model Series Hobby Stocks, Stock Cars, B Modifieds | Results | | Jason O'Brien (Dirt Super Late Models) | 5th | - | - | 9th |
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| 9/4/2020 | 300 Raceway - Farley, IA 43rd Annual Done Right.TV Yankee Dirt Track Classic Dirt Super Late Models: SLMR Late Model Series Stock Cars, A Modifieds, B Modifieds | Results | | Jason O'Brien (Dirt Super Late Models) | 4th | - | 2nd | 26th |
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| 9/5/2020 | 300 Raceway - Farley, IA 43rd Annual Done Right.TV Yankee Dirt Track Classic Dirt Super Late Models: SLMR Late Model Series Stock Cars, A Modifieds, B Modifieds | Results | | Jason O'Brien (Dirt Super Late Models) | 6th | - | - | 22nd |
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