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| 4/17/2021 | Maquoketa Speedway - Maquoketa, IA Season Opener w/ Midwest Jalopies Pro Legends, Vintage Modifieds, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Cole O'Brien (Pro Legends) | 5th | - | - | 10th |
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| 4/24/2021 | Maquoketa Speedway - Maquoketa, IA Weekly Racing $250 to win Sport Compacts Pro Legends, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Cole O'Brien (Pro Legends) | 1st | - | - | 2nd |
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| 5/1/2021 | Maquoketa Speedway - Maquoketa, IA Weekly Racing Pro Legends, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Cole O'Brien (Pro Legends) | 2nd | - | - | 10th |
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| 5/7/2021 | Hawkeye Downs Speedway - Cedar Rapids, IA Weekly Friday Night Racing - Opening Night Hobby Stocks, Sportsmans, Masters Legends, Hornets, Asphalt Sport Mods | Results | | Cole O'Brien (Masters Legends) | 5th | - | - | 5th |
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| 5/14/2021 | Hawkeye Downs Speedway - Cedar Rapids, IA Weekly Friday Night Racing Asphalt Late Models, Hobby Stocks, Sportsmans, Masters Legends, Hornets, Asphalt Sport Mods | Results | | Cole O'Brien (Masters Legends) | 1st | - | - | - |
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| 5/15/2021 | Maquoketa Speedway - Maquoketa, IA Weekly Racing $750 to win IMCA Stock Cars Pro Legends, Vintage Modifieds, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Cole O'Brien (Pro Legends) | 1st | - | - | 9th |
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| 5/21/2021 | Hawkeye Downs Speedway - Cedar Rapids, IA Weekly Friday Night Racing Asphalt Late Models, Hobby Stocks, Sportsmans, Masters Legends, Hornets, Asphalt Sport Mods | Results | | Cole O'Brien (Masters Legends) | - | - | - | 10th |
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| 5/22/2021 | Maquoketa Speedway - Maquoketa, IA Weekly Racing w/ AIRS Pro Legends, Vintage Full Body Stock Cars, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Cole O'Brien (Pro Legends) | 1st | - | - | 5th |
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| 5/29/2021 | Maquoketa Speedway - Maquoketa, IA Weekly Racing w/ School Bus Races Pro Legends, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Cole O'Brien (Pro Legends) | 1st | - | - | 3rd |
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| 6/5/2021 | Maquoketa Speedway - Maquoketa, IA Weekly Racing $1000 to win INEX Legends Pro Legends, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Cole O'Brien (Pro Legends) | 4th | - | - | 7th |
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| 6/11/2021 | Hawkeye Downs Speedway - Cedar Rapids, IA Weekly Friday Night Racing Hobby Stocks, Masters Legends, Hornets, Asphalt Sport Mods | Results | | Cole O'Brien (Masters Legends) | 1st | - | - | 8th |
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| 6/12/2021 | Maquoketa Speedway - Maquoketa, IA Del Gade Memorial Race w/ AIRS Pro Legends, Vintage Full Body Stock Cars, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Cole O'Brien (Pro Legends) | 1st | - | - | 5th |
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| 6/18/2021 | Hawkeye Downs Speedway - Cedar Rapids, IA Weekly Friday Night Racing Hobby Stocks, Sportsmans, Masters Legends, Vintage Full Body Stock Cars, Hornets, Asphalt Sport Mods | Results | | Cole O'Brien (Masters Legends) | 6th | - | - | 9th |
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| 6/25/2021 | Hawkeye Downs Speedway - Cedar Rapids, IA Weekly Friday Night Racing - MidSeason Champ Asphalt Late Models, Hobby Stocks, Sportsmans, Masters Legends, Hornets, Asphalt Sport Mods | Results | | Cole O'Brien (Masters Legends) | - | - | - | 8th |
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| 7/3/2021 | Maquoketa Speedway - Maquoketa, IA Weekly Racing w/ Bus Races Pro Legends, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Cole O'Brien (Pro Legends) | 1st | - | - | 4th |
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| 7/11/2021 | Benton County Speedway - Vinton, IA Urbana 5 - Weekly IMCA Racing Plus Legends Cars Pro Legends, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Cole O'Brien (Pro Legends) | 5th | - | - | 6th |
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| 7/16/2021 | Hawkeye Downs Speedway - Cedar Rapids, IA Weekly Friday Night Racing Hobby Stocks, Sportsmans, Masters Legends, Hornets | Results | | Cole O'Brien (Masters Legends) | 6th | - | - | 8th |
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| 7/17/2021 | Maquoketa Speedway - Maquoketa, IA Weekly Racing $500 to win IMCA Hobby Stocks Pro Legends, Vintage Modifieds, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Cole O'Brien (Pro Legends) | 4th | - | - | 8th |
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| 7/23/2021 | Hawkeye Downs Speedway - Cedar Rapids, IA Weekly Friday Night Racing Hobby Stocks, Sportsmans, Masters Legends, Hornets, Asphalt Sport Mods | Results | | Cole O'Brien (Masters Legends) | 4th | - | - | 2nd |
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| 7/29/2021 | Maquoketa Speedway - Maquoketa, IA Jackson County Fair Race Pro Legends, Vintage Full Body Stock Cars, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Cole O'Brien (Pro Legends) | 4th | - | - | 6th |
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| 7/30/2021 | Hawkeye Downs Speedway - Cedar Rapids, IA Weekly Friday Night Racing - COPS Night Hobby Stocks, Sportsmans, Masters Legends, Hornets, Asphalt Sport Mods | Results | | Cole O'Brien (Masters Legends) | 1st | - | - | 9th |
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| 8/1/2021 | Benton County Speedway - Vinton, IA Weekly IMCA Racing Plus Legends Cars Pro Legends, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Cole O'Brien (Pro Legends) | 8th | - | - | 11th |
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| 8/6/2021 | Hawkeye Downs Speedway - Cedar Rapids, IA Weekly Friday Night Racing Hobby Stocks, Sportsmans, Masters Legends, Vintage Full Body Stock Cars, Hornets, Asphalt Sport Mods | Results | | Cole O'Brien (Masters Legends) | 6th | - | - | 2nd |
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| 8/7/2021 | Maquoketa Speedway - Maquoketa, IA Iowa Donor Network Hall of Fame Night $1000 to win IMCA Modifieds $750 to win IMCA SportMods Pro Legends, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Cole O'Brien (Pro Legends) | 2nd | - | - | 13th |
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| 8/13/2021 | Hawkeye Downs Speedway - Cedar Rapids, IA Weekly Friday Night Racing Asphalt Late Models, Hobby Stocks, Sportsmans, Masters Legends, Hornets, Asphalt Sport Mods | Results | | Cole O'Brien (Masters Legends) | 5th | - | - | 7th |
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| 8/14/2021 | Maquoketa Speedway - Maquoketa, IA Season Championship w/ Bus ROC Pro Legends, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Cole O'Brien (Pro Legends) | 6th | - | - | 7th |
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| 8/15/2021 | Benton County Speedway - Vinton, IA Weekly IMCA Racing Plus Micro Mods & Legends Pro Legends, Dwarf, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Hobby Stock, IMCA Sport Compact | Results | | Cole O'Brien (Pro Legends) | 4th | - | - | 19th (DNF) |
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| 8/20/2021 | Hawkeye Downs Speedway - Cedar Rapids, IA Weekly Friday Night Racing - Season Championships Hobby Stocks, Sportsmans, Young Guns, Masters Legends, Hornets, Asphalt Sport Mods | Results | | Cole O'Brien (Masters Legends) | - | - | - | 6th |
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