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| 3/20/2021 | Brownstown Speedway - Brownstown, IN Indiana Icebreaker (Finished on 9/23/21) Dirt Super Late Models: Lucas Oil Late Model Dirt Series Dirt Late Models, CRUSA Dirt Late Models | Results | | Devin Gilpin (Dirt Super Late Models) | 9th | - | - | - |
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| 5/1/2021 | Florence Speedway - Walton, KY 35th Annual Ralph Latham Memorial Dirt Super Late Models: Lucas Oil Late Model Dirt Series DIRTcar UMP Modifieds: Summit American Modified Series Dirt Late Models, CRUSA Dirt Late Models | Results | | Devin Gilpin (Dirt Super Late Models) | 4th | - | - | 17th |
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| 5/12/2021 | Brownstown Speedway - Brownstown, IN Dirt Super Late Models: Castrol FloRacing Night in America DIRTcar UMP Modifieds | Results | | Devin Gilpin (Dirt Super Late Models) | 4th | - | - | 20th |
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| 5/22/2021 | Lake Cumberland Speedway - Somerset, KY Johnny Wheeler Memorial Dirt Super Late Models: Iron-Man Late Model Series | Results | | Devin Gilpin (Dirt Super Late Models) | - | - | - | 1st |
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| 6/15/2021 | Brownstown Speedway - Brownstown, IN DIRTCAR SUMMER NATIONALS DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals | Results | | Devin Gilpin (DIRTcar Late Models) | 3rd | - | - | 5th |
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| 6/25/2021 | Atomic Speedway - Chillicothe, OH 410 Sprints - Winged: OVSCA-Ohio Valley Sprint Car Association Dirt Super Late Models: Iron-Man Late Model Series | Results | | Devin Gilpin (Dirt Super Late Models) | - | - | - | 3rd |
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| 6/26/2021 | Atomic Speedway - Chillicothe, OH Dirt Super Late Models: Iron-Man Late Model Series | Results | | Devin Gilpin (Dirt Super Late Models) | - | - | - | 2nd |
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| 7/4/2021 | Lake Cumberland Speedway - Somerset, KY Beckley USA 100 Dirt Super Late Models: Iron-Man Late Model Series | Results | | Devin Gilpin (Dirt Super Late Models) | - | - | - | 4th |
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| 7/14/2021 | Circle City Raceway - Indianapolis, IN DIRTCar Summer Nationals - Super Late Models, UMP Modifieds DIRTcar Late Models: DIRTcar Summer Nationals DIRTcar UMP Modifieds: DIRTcar Modified Nationals | Results | | Devin Gilpin (DIRTcar Late Models) | 1st | - | - | 7th |
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| 7/23/2021 | Ponderosa Speedway - Junction City, KY Johnny Mulligan Classic Dirt Super Late Models: Iron-Man Late Model Series | Results | | Devin Gilpin (Dirt Super Late Models) | - | - | - | 22nd |
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| 8/6/2021 | Ponderosa Speedway - Junction City, KY Dirt Super Late Models: Iron-Man Late Model Series | Results | | Devin Gilpin (Dirt Super Late Models) | - | - | - | 18th |
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| 8/7/2021 | Brownstown Speedway - Brownstown, IN Dirt Super Late Models: Iron-Man Late Model Series | Results | | Devin Gilpin (Dirt Super Late Models) | - | - | - | 3rd (DNF) |
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| 8/13/2021 | Florence Speedway - Walton, KY 39th Annual Sunoco North/South 100 Dirt Super Late Models: Lucas Oil Late Model Dirt Series Dirt Late Models, CRUSA Dirt Late Models | Results | | Devin Gilpin (Dirt Super Late Models) | 2nd | - | - | - |
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| 8/14/2021 | Florence Speedway - Walton, KY 39th Annual Sunoco North/South 100 Dirt Super Late Models: Lucas Oil Late Model Dirt Series Dirt Late Models, CRUSA Dirt Late Models | Results | | Devin Gilpin (Dirt Super Late Models) | - | - | 1st | 26th |
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| 8/27/2021 | Moler Raceway Park - Williamsburg, OH 14th annual Victor "Ike" Moler Memorial Dirt Super Late Models: Iron-Man Late Model Series | Results | | Devin Gilpin (Dirt Super Late Models) | - | - | - | 2nd |
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| 8/28/2021 | Lake Cumberland Speedway - Somerset, KY 10th Annual Harold Hardgrove Memorial Dirt Super Late Models: Iron-Man Late Model Series | Results | | Devin Gilpin (Dirt Super Late Models) | 2nd | - | - | 3rd |
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| 9/11/2021 | Lincoln Park Speedway - Putnamville, IN Patriot 100 DIRTcar UMP Modifieds, Factory Stocks, 410 Sprints - Non-Winged, Super Stocks | Results | | Devin Gilpin (DIRTcar UMP Modifieds) | 1st | - | - | 1st |
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| 9/18/2021 | Lake Cumberland Speedway - Somerset, KY Mod Mania Dirt Super Late Models: Iron-Man Late Model Series A Modifieds: Iron-Man Modified Series | Results | | Devin Gilpin (Dirt Super Late Models) | - | - | - | DNS |
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| 9/23/2021 | Brownstown Speedway - Brownstown, IN Indiana Icebreaker (Continued from 3/20/21) Dirt Super Late Models: Lucas Oil Late Model Dirt Series Dirt Late Models, CRUSA Dirt Late Models | Results | | Devin Gilpin (Dirt Super Late Models) | - | - | 4th | 21st |
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| 9/24/2021 | Brownstown Speedway - Brownstown, IN Night Before the Jackson Dirt Super Late Models: Lucas Oil Late Model Dirt Series DIRTcar UMP Modifieds, Dirt Late Models, CRUSA Dirt Late Models | Results | | Devin Gilpin (Dirt Super Late Models) | 2nd | - | - | 18th |
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| 9/25/2021 | Brownstown Speedway - Brownstown, IN 42nd Annual Jackson 100 Dirt Super Late Models: Lucas Oil Late Model Dirt Series DIRTcar UMP Modifieds, Dirt Late Models, CRUSA Dirt Late Models | Results | | Devin Gilpin (Dirt Super Late Models) | 4th | - | - | 17th |
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| 10/15/2021 | Portsmouth Raceway Park - Portsmouth, OH 41st Annual Dirt Track World Championship Dirt Super Late Models: Lucas Oil Late Model Dirt Series DIRTcar UMP Modifieds, Pro Legends, Economy Late Models, CRUSA Dirt Late Models | Results | | Devin Gilpin (Dirt Super Late Models) | - | - | - | - |
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| 10/16/2021 | Portsmouth Raceway Park - Portsmouth, OH 41st Annual Dirt Track World Championship Dirt Super Late Models: Lucas Oil Late Model Dirt Series DIRTcar UMP Modifieds, Pro Legends, Economy Late Models, CRUSA Dirt Late Models | Results | | Devin Gilpin (Dirt Super Late Models) | 2nd | - | - | 25th |
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