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| 3/20/2021 | Whynot Motorsports Park - Meridian, MS MSCCS Late Models plus Weekly Racing Series Midgets, Dirt Super Late Models, Factory Stocks, A Modifieds, Pony Stock, CRUSA Street Stocks, CRUSA Dirt Late Models, CRUSA Late Model Sportsman | Results | | Andrew Boleware (CRUSA Street Stocks) | 8th | - | - | DNS |
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| 4/3/2021 | Whynot Motorsports Park - Meridian, MS Weekly Racing Series Event Factory Stocks, A Modifieds, Pony Stock, CRUSA Street Stocks, CRUSA Dirt Late Models, CRUSA Late Model Sportsman | Results | | Andrew Boleware (CRUSA Street Stocks) | 5th | - | - | 5th |
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| 4/17/2021 | Whynot Motorsports Park - Meridian, MS Weekly Racing Series Event Factory Stocks, A Modifieds, Pony Stock, CRUSA Street Stocks, CRUSA Dirt Late Models, CRUSA Late Model Sportsman | Results | | Andrew Boleware (CRUSA Street Stocks) | 5th | - | - | 8th |
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| 5/1/2021 | Pike County Speedway - Magnolia, MS Weekly Racing With Sprint Cars DIRTcar UMP Modifieds, Dirt Cage Kart Junior 1, Dirt Cage Kart Junior 2, 470 Sprints - Winged, CRUSA Street Stocks, Limited Modified, Limited Sport Mod, Pure Stock, Dirt Crate Late Models | Results | | Andrew Boleware (CRUSA Street Stocks) | - | - | - | - |
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| 5/8/2021 | Whynot Motorsports Park - Meridian, MS Weekly Racing Series Event Factory Stocks, A Modifieds, Pony Stock, CRUSA Street Stocks, CRUSA Dirt Late Models, CRUSA Late Model Sportsman | Results | | Andrew Boleware (CRUSA Street Stocks) | 4th | - | - | 4th |
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| 6/5/2021 | Jackson Motor Speedway - Byram, MS 16th Annual USCS Sprint Car Speedweek Finale 360 Sprints - Winged: USCS United Sprint Car Series Factory Stocks, CRUSA Street Stocks, CRUSA Dirt Late Models, Sport Compact, CRUSA Late Model Sportsman | Results | | Andrew Boleware (CRUSA Street Stocks) | 2nd | - | - | 2nd |
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| 6/12/2021 | Jackson Motor Speedway - Byram, MS Weekly Racing Factory Stocks, CRUSA Street Stocks, CRUSA Dirt Late Models, Sport Compact, CRUSA Late Model Sportsman | Results | | Andrew Boleware (CRUSA Street Stocks) | 2nd | - | - | 3rd |
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| 6/26/2021 | Whynot Motorsports Park - Meridian, MS Weekly Racing Series Event Factory Stocks, A Modifieds, Pony Stock, CRUSA Street Stocks, CRUSA Dirt Late Models, CRUSA Late Model Sportsman | Results | | Andrew Boleware (CRUSA Street Stocks) | 5th | - | - | 12th |
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| 7/3/2021 | Whynot Motorsports Park - Meridian, MS Prelude to the Southern Street Stock Nationals Factory Stocks, A Modifieds, Pony Stock, CRUSA Street Stocks, CRUSA Dirt Late Models, CRUSA Late Model Sportsman | Results | | Andrew Boleware (CRUSA Street Stocks) | 2nd | - | - | 10th |
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| 7/4/2021 | Magnolia Motor Speedway - Columbus, MS Firecracker 5 Finale 360 Sprints - Winged: USCS United Sprint Car Series Factory Stocks, Winged A-Class, Dirt Late Models, Hornets, CRUSA Street Stocks, CRUSA Dirt Late Models, CRUSA Modified Sportsman, CRUSA Late Model Sportsman | Results | | Andrew Boleware (CRUSA Street Stocks) | 7th | - | - | 18th |
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| 8/21/2021 | Jackson Motor Speedway - Byram, MS Weekly Racing Factory Stocks, CRUSA Street Stocks, CRUSA Dirt Late Models, Sport Compact, CRUSA Late Model Sportsman | Results | | Andrew Boleware (CRUSA Street Stocks) | 4th | - | - | 6th |
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| 9/11/2021 | Jackson Motor Speedway - Byram, MS KMSA and Weekly Racing Factory Stocks, Stock Cars, CRUSA Street Stocks, CRUSA Dirt Late Models, Sport Compact, CRUSA Late Model Sportsman | Results | | Andrew Boleware (CRUSA Street Stocks) | 2nd | - | - | 1st |
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| 9/18/2021 | Jackson Motor Speedway - Byram, MS Weekly Racing DIRTcar UMP Modifieds, Factory Stocks, CRUSA Street Stocks, CRUSA Dirt Late Models, Sport Compact, CRUSA Late Model Sportsman | Results | | Andrew Boleware (CRUSA Street Stocks) | 5th | - | - | 5th |
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| 10/8/2021 | Jackson Motor Speedway - Byram, MS All American 60 - Night 1 Factory Stocks, Winged A-Class, CRUSA Street Stocks, CRUSA Dirt Late Models, Sport Compact, CRUSA Late Model Sportsman | Results | | Andrew Boleware (CRUSA Street Stocks) | 1st | - | - | - |
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| 10/9/2021 | Jackson Motor Speedway - Byram, MS All American 60 - Night 2 Factory Stocks, Dirt Late Models, CRUSA Street Stocks, CRUSA Dirt Late Models, Sport Compact, CRUSA Late Model Sportsman | Results | | Andrew Boleware (CRUSA Street Stocks) | 1st | - | - | 5th |
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| 10/21/2021 | Whynot Motorsports Park - Meridian, MS 27th Annual Coors Light Fall Classic (Practice Night) Dirt Super Late Models, Factory Stocks, A Modifieds, CRUSA Street Stocks, CRUSA Dirt Late Models, CRUSA Late Model Sportsman | Results | | Andrew Boleware (CRUSA Street Stocks) | - | - | - | - |
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| 10/22/2021 | Whynot Motorsports Park - Meridian, MS 27th Annual Coors Light Fall Classic (Night 1) Dirt Super Late Models, Factory Stocks, A Modifieds, CRUSA Street Stocks, CRUSA Dirt Late Models, CRUSA Late Model Sportsman | Results | | Andrew Boleware (CRUSA Street Stocks) | 3rd | - | - | - |
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| 10/23/2021 | Whynot Motorsports Park - Meridian, MS 27th Annual Coors Light Fall Classic (Night 2) Dirt Super Late Models, Factory Stocks, A Modifieds, Pony Stock, CRUSA Street Stocks, CRUSA Dirt Late Models, CRUSA Late Model Sportsman | Results | | Andrew Boleware (CRUSA Street Stocks) | - | - | - | 14th |
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