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| 5/7/2021 | Outagamie Speedway - Seymour, WI 2021 Season Opener by Klink Equipment Street Stocks, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Sport Compact | Results | | Reagan May (IMCA Northern SportMod) | 8th | - | 8th | - |
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| 5/14/2021 | Outagamie Speedway - Seymour, WI Street Stocks, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Sport Compact | Results | | Reagan May (IMCA Northern SportMod) | 7th | - | 7th | - |
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| 5/16/2021 | Luxy Raceway - Luxemburg, WI Season Opener - 2021 COVID Crusher Part Two Street Stocks, Sport Compact, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car | Results | | Reagan May (IMCA Northern SportMod) | 5th | - | - | 11th |
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| 5/29/2021 | 141 Speedway - Maribel, WI Nathan Bouche Memorial / $1,000.00 to Win Stock Cars Triple Creek Series / 141 Championship Cup #7 Stock Cars, Sportsmans, Sport Compact, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car | Results | | Reagan May (IMCA Northern SportMod) | 8th | - | 8th | - |
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| 6/4/2021 | Outagamie Speedway - Seymour, WI Old Glory Honor Flight Night at the Races/Police, Fire & EMS Night at the Races Street Stocks, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Sport Compact | Results | | Reagan May (IMCA Northern SportMod) | 7th | - | 8th | - |
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| 6/12/2021 | Escanaba Motor Speedway - Escanaba, MI UPIR Fan Appreciation Week Presented by EMP Winged Outlaw, B Modifieds, Street Stocks, Vintage Full Body Stock Cars, Vintage Modifieds, Junior Sprints, Sportsman Micros, Sport Compact | Results | | Reagan May (B Modifieds) | 1st | - | - | 5th |
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| 6/25/2021 | Outagamie Speedway - Seymour, WI 5 Divisions of FRIDAY NIGHT THUNDER Street Stocks, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Sport Compact | Results | | Reagan May (IMCA Northern SportMod) | 4th | - | - | 14th |
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| 7/2/2021 | Outagamie Speedway - Seymour, WI SPEED & FIREWORKS on Independence Day Weekend at Outagamie Speedway Street Stocks, IMCA Northern SportMod, IMCA Stock Car, IMCA Sport Compact | Results | | Reagan May (IMCA Northern SportMod) | 4th | - | 2nd | 18th |
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| 8/6/2021 | Outagamie Speedway - Seymour, WI FIVE TO THE CROWN Street Stocks, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Sport Compact | Results | | Reagan May (IMCA Northern SportMod) | 4th | - | - | 17th |
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| 8/13/2021 | Outagamie Speedway - Seymour, WI Four to go.... Street Stocks, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Sport Compact | Results | | Reagan May (IMCA Northern SportMod) | 4th | - | - | 16th |
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| 8/15/2021 | Luxy Raceway - Luxemburg, WI Gandrud Auto Group Presents: Back to School Night featuring Backpack Giveaway Street Stocks, Sport Compact, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car | Results | | Reagan May (IMCA Northern SportMod) | 6th | - | - | 10th |
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| 8/20/2021 | Outagamie Speedway - Seymour, WI Two down, Three to go Street Stocks, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car, IMCA Sport Compact | Results | | Reagan May (IMCA Northern SportMod) | 6th | - | 2nd | 16th |
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| 8/29/2021 | Luxy Raceway - Luxemburg, WI Championship Night Street Stocks, Sport Compact, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car | Results | | Reagan May (IMCA Northern SportMod) | 4th | - | - | 12th |
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| 9/17/2021 | Escanaba Motor Speedway - Escanaba, MI 2021 Yooper Fall Classic Winged Outlaw, B Modifieds, Street Stocks, Non-Winged Sprints, Vintage Full Body Stock Cars, Vintage Modifieds, Generic 1, Sportsman Micros, Sport Compact, IMCA Modified | Results | | Reagan May (B Modifieds) | 2nd | - | - | - | | Reagan May (IMCA Modified) | 4th | - | - | - |
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| 9/18/2021 | Escanaba Motor Speedway - Escanaba, MI 2021 Yooper Fall Classic Winged Outlaw, B Modifieds, Street Stocks, Non-Winged Sprints, Vintage Full Body Stock Cars, Vintage Modifieds, Junior Sprints, Generic 1, Sportsman Micros, Sport Compact, IMCA Modified | Results | | Reagan May (B Modifieds) | - | - | - | 16th | | Reagan May (IMCA Modified) | - | - | - | 9th |
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| 10/2/2021 | Luxy Raceway - Luxemburg, WI The Return of the Fall Classic in the 'Burg Street Stocks, Baby Grand, Sport Compact, IMCA Modified, IMCA Northern SportMod, IMCA Stock Car | Results | | Reagan May (IMCA Northern SportMod) | 2nd | - | - | 8th |
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